


The Cutest Thing Ever

by NathanMonroe



Series: All-Daddy [3]
Category: Original Work
Genre: Age Difference, Asian Character(s), Beach Sex, Blow Jobs, Cheating, Extremely Dubious Consent, F/F, F/M, Female Ejaculation, Gangbang, Gym Sex, Infidelity, Interracial Relationship, Lesbian Character, MILFs, Marijuana, Multi, Multiple Orgasms, Older Woman/Younger Man, Oral Sex, Pedophilia, Prostitution, Public Blow Jobs, Seduction, Threesome - F/F/M, Underage Drinking, Underage Drug Use, Underage Prostitution, Underage Sex
Language: English
Status: In-Progress
Published: 2020-10-10
Updated: 2021-01-04
Packaged: 2021-03-07 01:07:50
Rating: Explicit
Warnings: Underage
Chapters: 5
Words: 35,653
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26458444
Author URL: https://archiveofourown.org/users/NathanMonroe/pseuds/NathanMonroe
Summary: 13-year-old junior high dropout Nathan Monroe has finally left his miserable family life behind and ran away to live on his own in the vast seaside metropolis of Bay City, California. But finding work isn't easy for a boy of his age. Just when it seems Nathan will be spending his first night alone on the streets, a chance encounter with a beautiful woman eager for some big teenage cock opens him up to his best chance at making money: prostitution. Using his increasingly irresistible good looks, smooth charisma, and, of course, his natural endowment, Nathan has nothing between him and a hot meal and place to sleep except a stunning lineup of horny ladies... many well over twice his age.But that's only half the story. As summer draws to an end, Nathan finds himself soliciting his body to the ultimate demographic: rich spoiled college girls on the campus of Bay City University. What do good girl Helena and rebellious stoner April have in common? They're both sending their daddy's money into Nathan's pockets in exchange for a night with him!But all that will look like small potatoes when Nathan meets Victoria Tomerlin, leader of the sexiest sorority in California, who will charge him rent... in his own cum!
Relationships: Original Character(s)/Original Character(s), Original Female Character/Original Male Character
Series: All-Daddy [3]
Series URL: https://archiveofourown.org/series/1531778
Comments: 10
Kudos: 24





	1. Tina

**Summary for the Chapter:**

> Fresh out of seventh grade, thirteen-year-old Nathan Monroe strikes out on his own to live in beachside Bay City. But supporting himself proves to be a lot more difficult than he thinks, and he winds up on the brink of homelessness... until he meets the cheerful 31-year-old Asian beauty Tina Zhou, who may be willing to lend Nathan a hand if he can give her something good in return.

In the summertime, Bay City, California felt limitless.

Starting from the beaches, there was a rolling plain of sizzling pavement packed with tourist traps, hotdog stands, untouched patches of marsh crisscrossed by wooden piers and outlined by cobblestone walkways, all teeming with sun-baked people walking here and there in oversized sunglasses, branded hats, and loose t-shirts over their swimwear. Further in, the buildings began to sprout and the roads widened, leading into the metropolis of the city proper, where the beach was mostly only visible from the skyline. Beyond that was another ocean, a green, leafy one, expanding throughout the rest of the state, until the desert began to take over. The clear skies struck the land mercilessly with the direct power of the sun, but short, intense rainfalls revitalized everything within hours.

Then, as the hours grow heavier, an orange palette rises into the sky as if from the sea, and fills the gaps between the buildings and trees, and eventually, between the clouds as well. The orange deepens into red, and darkens into violet, until night falls. Meanwhile, the crowds outside grow denser and more excitable as bars and restaurants fill up for dinner, and parties beckon afterwards.

This was the evening atmosphere into which Nathan Monroe arrived, with all of six dollar bills and a backpack containing a fresh change of clothes and a water bottle to his name. He was thirteen years old, had just finished the seventh grade, and was now a junior high dropout, leaving the eighth grade untouched (apart from its girls). He traversed the streets familiarly, his knowledge of the city extending back since he was nine. His hair had grown rather long: he had eschewed the baseball cap of his preteen years with a wavy mop that wrapped across his forehead almost into his eyes, which gleamed sparkling blue as always, and gone also were the loose, light t-shirts of his middle school skater phase, replaced with a beige button-up shirt that was one size too small, clinging tightly to his lean, hard frame: clearly just a placeholder until he was ready to go shirtless on the beach. The shirt, as well as his sandals, were stolen, but his crisp black shorts he had already owned for some time.

Tonight was it. Nathan had journeyed into Bay City from the suburbs many times throughout his childhood, unburdened by any semblance of a real household… but, ironically, it was because of that negligence that he had decided this visit would be a permanent one, leaving his so-called parents behind to only fret about his absence for legal reasons.

He had saved up money for the last month or so of the school year; just a few hours before arriving in the city that night, he had discreetly used the house phone to call a taxi, and he had used almost all of that money to reach the city from Gainesville, leaving only his current six dollars remaining. It had been quite an investment for a teenager his age with no allowance, but it was better than making the trip to Bay City on foot, since he had pawned his board when his skater phase ended last year.

He had slipped out after a meager dinner while his father sat asleep in front of the trash-playing TV and his mother sat locked in the master bedroom chatting incessantly on the phone with her hyper-zealous friends. It was quite easy to leave unnoticed. If it hadn’t been, perhaps he would have had less reason to do so in the first place.

But he did have reason, and now here he was, in the first night of the rest of his life, completely devoid of any direction or support except for one golden instruction: get a job. To that end, he headed across town to Martina’s sandwich shop, which he hadn’t visited in quite some time.

In fact, he hadn’t visited it in rather _too_ long, because when he arrived, it was unrecognizable. He approached its doors with horror as he realized it had been bought out by a generic chain franchise. He scowled to himself, but, he thought, maybe this was better for him. Maybe a bland corporation would be more likely to hire someone his age?

Turns out they weren’t, and it very well may have been the other way around.

“Can I have a veggie melt with no mayo, please?” he asked the grim-faced man behind the counter. He looked around as his supper was prepared: there were only three other people in the brightly-lit shop, all sitting and eating spaced far away from each other. The walls were crammed with meaningless trinkets. Where was Martina now?

“That’ll be $5.75,” the man said, and Nathan blanched. He hadn’t even thought to check the price first. There was nothing else to do but slap all six of his dollars onto the counter.

“Hey, are you guys hiring?” he asked casually, wishing he could talk to anyone else but this particular guy.

“We’re always kind of hiring,” the man answered, handing Nathan his change. Then he stopped, and looked at him. “How old are you?”

“Thirteen.”

“Yeah… I don’t think you’re old enough to work here.”

“I mean I can just sweep and clean, anything really.”

“I just don’t think we’re allowed to hire kids your age. The only thing I can think of is to ask your parents to get in touch with our hiring manager.”

“Oh… okay. I’ll, uh… I’ll ask my mom.”

Nathan took his sandwich and shuffled out into the night. Suddenly, the warmly lit commotion of the beach district seemed a lot less festive and a lot more restricted, as if he was in the middle of a party he hadn’t been invited to. He took a few bites of his melt, lost his appetite, and stowed the rest into his backpack.

A quarter. That was the sum of his personal wealth--twenty-five cents--and it was almost ten o’clock at night. An anxious shiver ran through his bones against the warm sea air as he began wandering aimlessly through the crowds down the streets. Where was he going to sleep tonight? He was homeless!

Worry wracked him, but it was too early for despair yet. He was hardly sleepy, after all. He still had a few hours to look around and see what solutions he could find. And plus, he was attracting quite a few passing stares as he explored the city, walking its sidewalks and drifting closer to the metropolitan district. A teenager on his own was hardly unusual in a city like this, but most teens didn't look like Nathan. His adolescent growth spurt had begun, and he was fast approaching the coveted six-foot milestone, with a strapping coat of young muscle to match.

As he wandered near the business district, the crowds thinned out, and there was something of a quiet belt in between the beachfaring throngs and the city life. The air smelled slightly less of salt, and there was just a bit less sand stuck in the grains of the sidewalk.

It was almost 11pm when he turned a corner and the swish of a white sundress caught his eye in the light of a streetlamp. She was walking away from him halfway down the block, shiny straight black hair waving back and forth on her shoulders as she walked, purse hanging over one shoulder. Her loose sundress, made of delicate-looking lace, hung off of her shoulders recklessly, and although he couldn't quite tell from this distance, he was intrigued by the fact that this woman may very well have gone braless tonight: the only other things she seemed to have been wearing were sneakers. She turned into a local surfer shop. Eager to get a better look at her, he followed.

It was a run-of-the-mill tourist shop, with fake wooden walls and gaudy tiki decorations advertising all manner of Ron Jon and Salt Life merchandise. At this time of night, it was almost empty, with Nathan, his new muse, and the oblivious cashier (visibly waiting for their shift to end) being the only three in the store.

She was on the other side of the store, near the changing rooms in the back, hunching over a shelf of t-shirts. Her arms were folded tightly across her chest, and she was studying the shirts closely, clearly trying to make a decision from their selection.

Nathan casually walked on by, doing some studying of his own. She glanced up at him, gave him a casual smile, and looked back down at the shelf of shirts, picking one up curiously.

She was an extremely pretty porcelain Asian woman, although Nathan in all his whiteness couldn’t even begin to tell anything beyond that. Her cute jet-black hair was ruler-straight and tied back neatly in a ponytail, in an almost extreme contrast to her bright white skin, of which she was showing plenty.

But it was her dress that was catching Nathan’s eye… or rather, everything around it. Her chest, cleavage, shoulders, back: all untouched by the lace sundress.

“Hey, where’d you get that dress?” he asked her. He had to raise his voice slightly over the distance he was giving her.

She looked up at him, then down at herself. “Oh… sorry, my dress?”

“Yeah, I like it! Where did it come from?”

“Oh! I got it years ago, in Minnesota.” Her sweet dark eyes were round and rather wide from surprise at the question.

“Minnesota, okay! Can I look at it?”

“You want to… see my dress?” She put down the shirt she was holding and walked around the display towards him. She was only an inch or so taller than him. “What is your name?”

“I’m Nathan,” he said, holding out her hand.”

“Tina.” She smiled, and shook it. “Now why if I may ask are you so interested in this dress I’m wearing?” She spoke with a strained cadence that suggested English wasn’t her first language.

Nathan shrugged. “Maybe I’m not so interested in the dress by itself,” he teased, looking her up and down. “But it looks great on you!”

Tina giggled, waving her hand at him. “Oh, you are much too young to be saying things like this to me!”

“You want me to stop?” he asked slyly.

“No… I don’t mind.” She swayed a bit on her feet as she spoke, smiling bashfully. “But I do wonder, how old you are?”

“Thirteen.”

“Oh…” She nodded, processing the information.

“How old are you, Tina?”

“I am thirty-one. Nathan, are you here all by yourself?”

“Yeah,” he said suggestively. “I’m all alone.”

Now it was her who looked him up and down. “Where are your mother and father?”

“Gainesville,” he answered honestly.

“Gainesville?! But that is far away! Are you visiting someone here?”

“Maybe. Or maybe I just ran away from home.”

Tina gasped good-naturedly. “Oh no! You can’t run away! A young boy needs his parents!” But she was smiling all the same.

“I don’t need parents,” Nathan said, and now it was he who waved his hand at her. “I have...”

And suddenly he was gripped with an idea.

“...you.”

He took another look up and down her body. He could just barely see the slight indentations of her nipples against the fabric, but not much else.

“So, Tina,” he said, making conversation. “What were you looking at over here?”

He walked over to the shirt display he had found her at, and she followed him back to it.

“Oh, just looking for a fun shirt for my nephews back in Minnesota,” she said, standing very close to him next to the display. “These are all very expensive though!”

“Minnesota, that’s where you said your dress was from, right?” He reached up and gently stroked Tina’s bare shoulder with his fingertips, softly brushing the thin shoulder strap of her dress aside and dropping it down her arm.

“Oh… yes!” She laughed timidly, pulling her shoulder strap back up. “This dress that you like so much. Is it strange for a thirteen-year-old boy to take such interest in dresses?”

“Uh, it might be unusual, but I wouldn’t call it _strange_.”

They stood close enough together that their bodies were brushing on each other. Nathan was looking quite shamelessly down at Tina’s chest, but she wasn’t looking back at him to notice.

“So which shirt did you have your eye on?” he asked. “Any?”

“Hmm, well these here…” She leaned over to place a slender white hand on one of them, and her dress hung right down. “Maybe you can help me pick one out? You are not too much older than my nephews.”

Nathan looked down her loose top and could see clean through to her bright pink nipple, protruding from her petite breast in the shadows under her dress. As she moved about, her nipple rubbed against the inside of the lace fabric.

“I think you were right,” Nathan said, putting his hand on hers, gently moving her touch off of the shirts. “These cost way too much.”

She held his hand. “Yes… yes you’re right.” She looked at him with her big dark eyes, and he looked back at her, placing his hand on her back and rubbing slowly.

“You, uh, you like… you like to touch a lot?” she asked him.

He removed his hand from her back, but she kept her hold on his other one. “Yeah, is it okay?”

“Yes. It feels nice.”

He returned his hand to her back, rubbing more now, his fingers and palm sliding from the fabric of her dress, across her bare skin, and back again in a wide circle.

“But…” she chuckled a bit. “You are only thirteen! And you have run away from home, and touch strangers like this?”

“Mm-hmm.”

She paused for a moment.

“Did you… still want to look at my dress?”

“Yeah…” Nathan glanced over his shoulder at the cashier on the other side of the store, who so far had spent the entire time glued to their desk computer.

“Let’s go back here,” he said, guiding her by the hand into the little nook behind the sales floor, in front of the changing booths.

“Yes, this is a good place,” she said, looking around and placing her purse on the floor. “It is out of the way.” Then she spread her arms and looked at him. “Well here I am! You can look at me.”

“You’re totally beautiful, Tina,” Nathan remarked, smiling at her.

“Thank you! You are a very nice and handsome young man.”

“You wear this dress because it’s hot outside?” he asked her, stepping closer and touching her arm. “Because it doesn’t cover everything up?”

“Yes, it leaves a lot exposed,” she agreed, watching his hand glide up her arm to her shoulder.

“But are you afraid of, like, your boobs showing by accident?” He had both his hands on her shoulders, like a school dance.

“My boobs?” she repeated unsurely. “You mean… here?” She placed her hands on her breasts, holding them through her dress.

“Yeah, like see, if it did something like this…”

Nathan reached around, pulling up the rear hem of her dress so that it covered her back, and her shoulder straps hung down past her armpits. The front of the dress now dangled low and her full breasts peered out from above the collar, only the bottom curve still hidden behind the fabric.

“See? Like it could do that by accident, right?”

“Oh!” Tina looked down at her bare breasts now pointing out at him. “No, that has never happened.”

“You know, I could see them out there when we were looking at those shirts.”

“You could see my breasts out there?! Oh, how embarrassing! I had no idea.”

“Are you embarrassed by me looking at them right now?” He pulled her dress back up to cover her. “I could put them away…?”

She shook her head. “You can look at them if you want,” she said, pulling the dress back down for him, showing him her breasts. “I know you are a very… attracted young man. You like looking at these things.” She glanced over her shoulder nervously, but they were alone. “But, it’s illegal! You’re underage.”

“Want to go into a changing room?” Nathan said, reaching over and easing one of the thin wooden doors open. Beyond was a tiny closet-sized space with a bench and a wall mirror.

“That would be a good idea,” she admitted, picking up her purse, and Nathan pulled her by the hand into the little booth, locking the door behind them.

“Nathan…” she said, taking both his hands in hers. Her breasts showed casually above her dangling dress. “Sorry, I must ask… did you talk to me because you could see into my dress?”

Nathan grew slightly red in the face. “I just wanted to see them.”

“Do you like them?”

“Yeah. Can I touch them?”

“Yes.”

Nathan dropped his backpack onto the floor and put his hands on her breasts, feeling them fully in his palms. She suddenly shuddered, and he felt that instinctive electricity bloom in between them. Nathan pulled her into him for a kiss, and she responded passionately, scooping his head in her hands and moaning lustfully, like so many repressed feelings had finally been let free. He stuck his tongue into her mouth and she sucked it, and his erection pressed onto her through his shorts. They swayed together like that for a while before breaking apart breathlessly.

“Oh Nathan!” she cried, looking down. “You have a big cock!” She grabbed it and started rubbing it through his shorts.

Nathan gave her nipples a little pinch. “Ten bucks and I’ll let you suck it.”

“Ten dollars? Yes! I will!” Tina dove for her purse, fishing out her wallet and handing Nathan a ten-dollar bill. He stuck it in his pocket, and she sat down on the little changing room bench as he unzipped his shorts and pulled out his penis, letting it stand high and hard in front of her face.

Nathan hadn't just grown in height during the seventh grade: his pubescent growth spurt was also hitting his genitals, and now his fully erect penis was a complete ten inches long. Tina grabbed it immediately, breathing in its strong scent.

“You are a giant!” she exclaimed, and began jacking him off with both hands.

“Your hands are so smooth!” Nathan responded as Tina stuck his cock into her mouth and began sucking. He held her shoulder straps as she sucked, and slipped them off. She let go of him briefly to pull her arms out, letting the dress fall down around her waist and leaving her topless. He felt her tits as she quickly grabbed him again and kept sucking, her drool landing on his hands and her chest as she slobbered all down his length with true enthusiasm. Her petite frame made him look even bigger, and she slurped and licked on him like she was already in love.

“Fuuuuck…” Nathan groaned, leaning back a bit, pushing his hips out towards her as he felt his head jamming into her throat.

She popped his length out of her mouth messily, spit coating his shaft, ropes of drool hanging between her lips and his foreskin. "You are so young!”

“You’re not my oldest, Tina,” he assured her. She stroked his dripping shaft, pulling his foreskin back and smearing her own saliva around on his tip.

“You have… girlfriend of your own age?”

“Yeah, lots.”

“Lots!” She plunged his cock back into her mouth and kept sucking passionately, pulling on him back and forth, massaging his head with her lips and tongue. “You charge too little!” she continued. “For such good cock! How much to come to my home with me?”

“Hmm…”

He had initially been planning to charge twenty dollars for sex, but now that she had said he was under-charging...

“Another thirty.”

“I will pay.” She resumed her sucking, and tingles began to run through Nathan’s balls and around his head. He breathed deeply, reaching down to feel Tina’s breasts some more, and her heavy licking and stroking coaxed out his load and he shot his cum directly into her mouth.

Tina moaned deeply and drank from his cock like a spigot, holding his shaft in both hands and chugging his cum as it poured into her mouth. The sensation inflamed Nathan, who gripped the base of his penis and trembled as his head burst in what felt like sparks of electricity inside Tina’s mouth.

She kept his drained cock in her mouth, sucking it softly, as Nathan recovered, panting heavily. Then she popped it out from between her lips and looked up at him, before reaching into her purse again and handing him a twenty.

“I have more money in my house,” she assured him, pulling her dress back up to cover herself. “I can bring you over, and give you the money?”

Nathan smiled, and tucked his cock back into his shorts, offering Tina his hand. “Lead the way.”

They grabbed their bags and walked back onto the sales floor, hand in hand, emerging out of the store onto the streets completely unnoticed. Tina was parked in a small gravel lot next to a burger join a couple of blocks away: she led him to her car and together they drove off towards her place, wherever that was. Nathan was utterly relaxed to the point where he was only kept awake by the bumps in the road, but Tina seemed live-wired, and couldn’t stop smiling the entire ride.

“Why you ran away, Nathan?” she asked him as she drove. “If it’s appropriate?”

Nathan shrugged, rubbing his eyes. The sleepiness was already beginning to wear off, and he could feel the aching emptiness in his testicles ease already, as they began to refill.

“I never had much of a relationship with my parents,” he said. “I kind of never had parents. I was raised by my girlfriends’ moms, you know, whenever I would stay over at a girl’s place growing up. And then my teachers were also like my moms. But my real mom, she just didn’t bother. So I left them, to have a life.”

“That is so sad!”

“Yeah… I guess. It worked out pretty well, I was really lucky to know a lot of other good families who let me spend time with them.”

Tina nodded, and seemed content with this. Privately, Nathan took a moment to assess his situation: he was now worth thirty dollars ($30.25, to be exact), with ten more promised to him: that would almost be enough to afford a motel room! If Tina let him sleep with her, he could spend tomorrow finding a new woman who could pay him the remaining money needed to afford his own place that night.

And to think he had started out with only six bucks a couple hours ago…

When Tina turned off the street, Nathan was surprised: she too was living in a hotel! It was a nice hotel that seemed mainly suited towards traveling businesspeople, but still, he had expected an apartment at least.

“Do you… still live in Minnesota?” he asked her as they parked.

“Oh no!” she said, turning off the car. “I live in Palo Alto, I am traveling statewide for work. I am a transaction coordinator for technologies.”

They got out of the car and Nathan followed her into the hotel. The lobby wasn’t too busy this time of night, but even if it had been, nobody would have thought twice about the pairing, which could have been any number of innocent things.

“What’s a transaction coordinator?” he asked her in the elevator.

“Well, large sums of money go from one firm to another. Sometimes I am needed to talk to both sides and make sure everything goes well, especially with other countries.”

The elevator dinged and the door slid open on the third floor. Tina’s room was a quaint and decent-sized one, facing away from the ocean but instead offering a nice view of inland Bay City.

“Be comfortable!” she exclaimed, taking off her sneakers. Nathan took off his sandals and placed them next to her shoes as she strolled briskly past the kitchen area to her bedroom.

“Please wait!” she said from the other room, and Nathan could hear her rummaging around. In a few moments she emerged again and handed him a ten-dollar bill. $40.25.

“There is your money, as promised!” she said cheerfully.

“Great!” Nathan stowed the cash in his backpack with the rest of his money. “Do you want me to come into the bedroom now?”

“Oh please! Everything is put away…” She brought him into the room and locked the door behind them. “Sorry. I did not want you to see my briefcase. Private materials.”

“Oh I get it, no problem,” Nathan said, sitting on the edge of the bed. Tina stood in front of him, looking excited but unsure. Her dress was a bit ruffled, showing more cleavage than she probably intended.

“I am going to… clean my mouth.” She blushed a bit, and ducked into the bathroom, keeping the door open as she began to brush her teeth.

“Do you want me to get naked?” Nathan asked her from the bed.

“Naked?! Oh!” Her squeak echoed slightly within the tile bathroom walls. She spat her toothpaste out. “Yes! I would like you to be naked. I will also undress here.”

Nathan heard her gargling mouthwash as he unbuttoned his shirt and tossed it aside onto the floor, then unbuckled his belt. He had just kicked his shorts off and gotten fully naked when Tina emerged back out of the bathroom also naked. They looked at each other and beamed: Nathan’s body was young, hard, fit, coated with tough lean teenage muscle, and his cock was already starting into another erection. Tina’s body was slim but soft, pale and smooth like her face, and a deep black bush sprouted between her legs.

“I would like to kiss you?” she said unsurely, and Nathan leaned back across the bed onto the pillows. Tina laid down next to him. They wrapped their arms around each other, intertwined themselves naked, with Nathan’s cock rubbing Tina’s soft black bush, and made out.

Nathan ran his hands all up and down her bare back, down to her ass, which he grabbed and squeezed. Tina gripped his back with her fingers right under his shoulder blades, and pressed her body tightly against his. His cock rubbed between her legs and he could feel the heat of her vagina on his shaft.

Their tongues danced around each other playfully, swirling and licking each other in between smacks of their lips as they pressed together and parted repeatedly. Nathan humped his cock against Tina’s labia, and he could feel her juices leaking onto him. She grabbed his cock as they kissed, sliding her hand up and down his ten-inch length, and he moved himself away from her, giving himself room to put his hand between her legs and rub her lips. Her body tensed, almost spasmed, and her nails dug into his back as he rubbed her soaking clit with his fingertips.

He pushed his fingers inside; they slid in easily. Tina gasped sharply, and they never once took their eyes off each other as Nathan curled his fingers and felt around for her special spot. She got wetter and wetter, drenching his hand and making a mess of her bedsheets. She squealed as she came, and Nathan moved down her body to begin sucking on her nipples, never moving his fingers out of her.

She held his head and cradled his face into her breasts, and he licked and sucked them greedily, slowly roving his fingers inside her.

He dragged his tongue around on her smooth clear skin, licking between her breasts, up across her chest, around on her shoulders. She moaned and squeezed him tight into her body, her soft thighs clamping onto his hand.

He pulled his fingers out and popped them into his mouth, sucking her juice off, and she grabbed his head and pulled him in for another kiss. He wedged his cock between her legs again, and she rolled over on him, pushing Nathan onto his back. They communicated wordlessly: he put his hands on her small pale butt and moved her up a bit on his body, and she reached down to hold his cock and position it between her legs. She dropped down on him and he glided into her with a noisy squelch, and they both cried out. She grabbed his hard young chest, her thighs clamping on either side of him, and she pushed herself down on him hard, engulfing his cock in her body.

She fucked him, grinding his cock on herself, and began moaning at him desperately in Mandarin. He kept his grip on her ass: she didn’t have much of one, but it still felt wonderful to rub and squeeze as she moved it back and forth on his groin.

She exploded on him, spraying his crotch with her juices, and she dove back down onto him to stick her tongue back into his mouth. He flung his arms around her shoulders and they tongue-kissed again, her pussy trembling all up his length, which throbbed stiff as a board inside of her.

Tina continued to rock herself on his cock as she kissed him eagerly, and he groaned into her mouth as he got closer. Her pussy rubbed him up and down, their hot skin plastered onto each other, and he released himself deep into her, shooting his load up her vagina.

Tina straightened up and threw her head back, feeling him fill her up, her eyes closed with euphoria.

“So big…” she moaned. “You are perfect, Nathan.”

She climbed off of him, curling up next to his lap and holding his drenched cock in her hand. “Let me suck.”

He stroked her shiny black hair as she began to slurp her own juices off of his head and shaft, cleaning up the swirling white cum that her pussy had massaged around on his skin.

She sucked him deep and long, keeping him hard as he relaxed back against the pillows and stroked her pale naked back. Her hands squeezed and rubbed his shaft, and her lips slid nicely up and down his length. She sucked and sucked, and he stayed stiff as a board inside her mouth, reaching around her shoulders, under her arm, holding her breast as she serviced him to her heart’s content, until her jaw started to ache.

Soon she slid his cock out of her mouth and looked up at him.

“Inside me again?” she asked. He nodded, and rose to his knees, putting his hand firmly but tenderly on her back and keeping her still as he got behind her. She wiggled her butt, bracing herself on her hands and knees and looking at him over her shoulder. He positioned himself on his knees, his cock bumping into her butt, and he held it steady and pushed it inside her.

Tina almost screamed. Before, when she was riding him, she had felt full. She had been connected to him, and their personal physical pleasures had entirely merged.

But now, as he entered her from behind, it was a whole new level of sensation. From that angle, his ten-inch cock seemed to break past all barriers to the epicenter of her body where sheer bliss was stored, and activate inside of her something bright and overwhelming. And as he held her steady and began to pump himself into her, all remaining walls between her and euphoria were shattered, and she began to cum incessantly on his shaft.

Nathan breathed deep and steady as he pushed in and out of Tina, focusing on the sensation of her pussy squeezed around his cock. He moved fairly slowly, gliding back and forth, feeling every wet hot inch of her and taking his time. Her back swayed before him, pure white and smooth as soft glass, and he ran his hand up and down it, feeling her skin under his fingers. She moaned and grabbed at her breasts: he understood the request and reached under her to grope her.

Squeezing her tits, his pounding grew faster and harder, and he kept feeling splashes of slick heat waving on his dick from inside of her.

He held onto her hips, leaning back, thrusting wildly. Pressure built up fast in his balls, and burst out of his cock in a bright spray of cum. He slammed himself into her, and she squealed and pushed her ass back against him, holding him inside as he shot his load.

Nathan fell back onto his hands, his hips pushed up into the air, his cock resting inside of Tina.

“Nathan…” Tina moaned, collapsing down onto her stomach. Nathan’s dick slid out of her and he lied down next to her. Tina rolled over and Nathan held her from behind, pushing his semi-flaccid penis against her flat butt and holding her breasts snugly as they spooned.

“Nathan…?” she said.

“Mm-hmm?”

“I was your first customer?”

“Yeah,” he said with a grin. She turned her head to see his smile.

“I will not be the last.” She gave him a peck on the mouth, and reached over to switch off the bedside lamp for the night.


	2. Julie

**Summary for the Chapter:**

> It's a beautiful day on the beaches of California! On the prowl for fresh tail, Nathan happens across the 30-year-old sunbathing beach bunny Julie Voss. Julie chose this secluded spot for a reason, and would prefer if no men tried to bother her... but she just might make an exception for this handsome thirteen-year-old.

Nathan walked along the tide in high spirits, his feet sinking into the wet sand and the sun shining down bright on him and everyone else enjoying the beach that day an hour or so after noon. He had on nothing but a pair of swimming trunks, and it felt liberating to finally explore the shoreline shirtless, no parents to return to, no rules at all except the laws of nature. His thirteen-year-old cock, almost six inches long even fully soft, swung boldly under the swimming trunks, and even though he hadn’t yet approached anyone close enough for them to notice what he was packing underneath, it still felt absolutely liberating.

Earlier that morning, he had been awoken by Tina Zhou, who ushered him out quickly as she finished preparing for work, giving him only enough time to use the bathroom and brush his teeth. His penis still smelled strongly of her and her cum had dried into a thin film on his shaft and head.

He had slipped out of the hotel with his backpack containing forty dollars in cash, spirits already high knowing that he need score only one trick today to afford a room of his own later on.

But who would it be?

He finished his deli sandwich from last night as his breakfast, and headed out to the sands of Bay City, stripping down to his swimming trunks and wearing his backpack across his lean bare shoulders. The beaches in this part of town were almost never slow: this early in the morning, the crowds were a bit smaller, but you couldn’t go ten feet without walking by a new person. This would have been ideal for Nathan’s search for a lay, but as it turned out, all of the hot girls he noticed were with other people: every time someone caught his eye, he saw her talking to some guy, or even a group of them.

A few times, when a girl caught his eye, he caught hers back. Holding a spontaneously tense eye contact with a random woman walking by was far from unfamiliar to Nathan, but right now he was on the hunt, and those kinds of things could mean the difference between him sleeping in a bed tonight, and being homeless.

At one point, he locked eyes with a beautiful young woman he spied about fifteen feet away from him, as he walked by. She was standing around with a scattered group of oblivious friends, all congregated next to their set of beach towels and coolers. They exchanged smiles; he slowed to a stop and winked at her, and she chuckled to herself privately, sticking her tongue out at him flirtatiously. She looked like a high school or college girl, maybe 17 years old, or even legal, with a long white body and a bright red strapless bikini that stood out against it, and wet brown hair that hung past her shoulders. She had a very pretty face with big eyes, and a simple necklace resting against her bare chest.

She and Nathan continued to hold eye contact as her friends chatted on around her. She took a few steps away from her friends as Nathan took a few steps toward her, cutting the distance between them roughly in half: close enough to talk if not for the risk of catching her friends’ attention. Her amused grin grew as the sexual tension between them rose, and when Nathan’s gaze fell from her face to her breasts, she was close enough to notice. She looked down at her own boobs, and looked back up at him, making an inquiring face. He answered simply by looking down at her breasts again; she walked away from her group, giving Nathan a little nod to follow her. He made a beeline around the group to meet up with her behind a wide beach umbrella that was leaning on its side, providing a tiny wall.

“Hey, were you looking at my tits?” she demanded of him, crossing her arms and hunching over slightly to make up for her greater teenage height.

“Uh… yeah.” Nathan gulped. Was she mad?

“What, did you come to the beach to look at girls’ boobs like a little pervert?”

Nathan shrugged, his face burning red. “I just thought you were really pretty and wanted to see your boobs.”

She stood up straighter and tilted her head, hesitating with surprise at his answer. Arms still crossed over her breasts, she looked up him and down curiously, her expression softening as she drank in his young, fit physique.

Finally she broke out into a smile, lowering her crossed arms.

“Well, at least you’re being cute about it,” she admitted. “Want to see them?”

“Will you show me them?” Nathan said, his face brightening. He was trying to act cool about it, but his excitement leaked through.

“Yeah,” she giggled, leaning her head back and pushing her hair behind her shoulders, clearing up her chest for a flash. Nathan flushed a bit from excitement: this was by far the fastest he had ever gone.

“Chelsea, where’d you go!?” a voice came calling from the gathering.

“I’m right here!” she called back, keeping still behind the scant privacy of the toppled beach umbrella: if either of them took a single step, they’d be visible.

“Wait, where?!”

Chelsea ignored her friends for the moment, looking back at Nathan. She flashed him, pulling her red bikini top down and showing him her breasts. They were pale, puffy, and conical: definitely the breasts of a girl on the younger side.

“You’re a horny little boy,” she remarked with a laugh, watching him stare at her exposed tits.

“Hot high school girls tend to do that to me,” he shot back smoothly, and she licked her lips at him.

“CHELSEA, LET’S GO!” another voice called suddenly.

“I’M COMING!” she cried, giving Nathan a wink as she pulled her top back up and ran back to meet her friends. It was only then that Nathan realized he had never even gotten the chance to ask for money. He stood there behind the toppled umbrella, horny and frustrated, and now a bit nervous. But the sun was still high, and he still had all day to make some more money.  
  
So he kept looking.

It wasn’t as if it was much of a chore: he was literally walking along the beach on a bright hot day, looking for girls. He just had to get past the hustle and bustle to a quieter part of the shoreline, away from all the groups and parties. Tina had been an example of a perk of the city’s tourist traffic; he was currently dealing with a downside: having to look for a woman he could talk to alone.

The beach curved, and he continued to follow it, shuffling his feet experimentally through the sand, feeling it morph and mold between his toes as he passed by the patches of tall grasses left standing by the tides. Way off in the distance were some of the skyscrapers that pushed through to the shore from the inner metropolis.

The beach was empty here, the sounds of activity fading behind him as he walked further and further, past an old pier with just a couple of people, all of them looking like actual residents. Further on, however, was a lone figure relaxing in the sand. He walked on, getting closer, and with every step he became more and more convinced that he had found his next trick.

Largely shielded from sight by sand dunes and tall wild reeds, she was sprawled out on her stomach across the sand, leaning on her elbows to watch the waves with smoldering blue eyes still clinging to the last of the eyeliner not washed away by her recent swim. She had a scrunchie on her wrist, leaving her jet-black hair loose to dry in the sun, a few strands crossing her stunning face: her cute little nose, her sharp eyebrows, and her chin and jaw that looked downright heroic. She was wearing a soaking white tank top and a black bikini bottom, and her long, slender legs, sun-kissed to match the rest of her body, swayed back and forth behind her as she relaxed alone on the beach, her firm ass pointing skywards. Nathan wouldn’t have been able to keep away from her even if he hadn’t been working. He approached her boldly, walking right up to her at full strolling speed, knowing full well she chose her spot specifically to be left alone from leering men: his two chances were his young age and the fact that he was hopefully not the kind of person this woman was trying to avoid.

“Just get done swimming?” he asked her as he approached, and the woman turned to look up at him.

“I did indeed,” she answered, with that familiar streak of uncertainty that grown women spoke with when he flirted with them. “Are you about to?”

“Maybe,” he said, standing over her. Her top was messily bunched up her torso, showing him her lower back, flecked with sand and glittering with sea salt. “How’s the water?”

“It’s nice. It’s a good day to be swimming.” She looked around the beach. “Are you here alone?”

“Mm-hmm.” He sat down next to her in the sand. “Are you?”

“Yeah. It’s nice to swim alone.”

“Ah. Well then I won’t be one more annoying boy trying to hit on you.” He stood up, betting his stakes.

“Well, hey now!” She stopped him, and his bluff paid off. “We can at least introduce ourselves, right? I’m Julie.”

“Nathan.” He sat back down next to her and shook her hand. “Let me guess, you’re a model.”

She laughed starkly. “I have modeled before, yes. But I am not a career model.”

“That’s insane, why not?”

She looked over at him, her amused expression shot through with skepticism. “Why aren’t you a career model, Nathan? You certainly look like one.”

“Who says I’m not?”

“Oh?” She arched her expressive brow playfully. “Who have you modeled for, then?”

It was a game, Nathan recognized. If this woman wasn’t flirting with him yet, she was as close as she could get.

So in response, he decided to push them a bit closer still.

“I’ll model for any lady who wants to look at me,” he answered with a sly shrug.

Julie blinked, momentarily frozen in surprise at his answer.

“Well,” she responded, regaining her composure and adjusting her position lying on the sand. “Let’s say I wanted to look at you some more. Would you model for me?”

“Definitely.”

“What are your rates?”

Nathan hesitated briefly. He had decided on his rates for sex earlier: ten dollars for first and second base, plus twenty for third, and finally another thirty for a home run. But that wouldn’t really fit into their joke, would it? He improvised fast: he knew that being witty and charming was just as important to picking up women, maybe even more so, as looking good for them.

“Depends on which parts of me you want to look at.”

Julie flinched and her sharp eyebrows rose, but she seemed impressed as much as shocked.

“You are trouble!” she remarked, a grin suddenly piercing her intense face. “How old are you?”

“Thirteen.”

“My god. And what is a thirteen-year-old model doing all by himself flirting with grown women?”

“Oh, are we flirting? Sorry, I didn’t know.”

Julie laughed again, but unlike last time, she had lost all skepticism. “You _are_ trouble! Are you really out here all alone?”

Nathan nodded reassuringly. “Nobody knows where I am.”

Julie nodded, and Nathan saw the spark flare in her simmering blue eyes as they looked into his. She leaned over on one elbow in the sand, freeing up her other hand to reach out and feel his firm chest.

“Thirteen, huh?”

“Yes, ma’am.” He scooted a bit closer to her, slipping off his backpack, and she ran her hand along his developing pectoral muscles, leaving a thin trail of damp sand across his skin.

“Well here’s what I think, Nathan.” She moved her hands down to his stomach, where her fingers traced his young abs which seemed to be growing in definition every day. She arched her eyebrows in approval of his physique.

I’m thirty,” she continued. “And I think that any boy your age who has the balls to come hit on a woman my age the way you did deserves to be treated like a man.” Her hand ventured lower, grazing the waistband of his trunks. “Especially a boy your age as fucking hot as you are.”

Nathan was growing hard, and fast. He took the waist of his trunks and pulled them out, leaving a gap for Julie to slide her hand right into.

“Oooohhh…” she groaned, grabbing his stiff cock as it reached full mast. He pulled it out for her, getting on his knees, his erection protruding right in front of Julie’s face.

“Oh yes, I knew you were huge,” she said with satisfaction, grabbing his cock and jerking him off. She looked around cautiously, prompting him to do the same: not only was this part of the beach empty, but they were walled off by sand deposits, fenced in by grasses. She kept stroking him as the waves crashed tranquilly beyond.

“I knew you had to be huge,” she continued. “Coming on to me the way you did. You know I’ve perved on younger boys before, but let me tell you, Nathan… none of them were ever nearly enough to get what they wanted from me.” She looked up at him with piercing bedroom eyes. “So good job there, baby.”

Nathan stroked her hair. “Ten bucks to keep jerking it.”

“Oh is that so?”

“Twenty to put it in your mouth, thirty to put it somewhere else.”

“Ah, I see.” She nodded her head teasingly, as if playing along with a game. “So if I did this…”

She gave the tip of his cock a full, sensual lick of her tongue.

“...I’d owe you twenty bucks?”

“You would.”

“Well I don’t have any money on me, baby,” she said, resuming her stroking. “So how about I pay you in arrears, give this gorgeous monster of yours some attention, then bring you home with me and see if we can’t get you some more business? Hmm?” She licked the tip of his cock again.

Nathan shivered in delight, wordlessly putting his hand on the back of Julie’s head and pushing her face down onto his cock. She groaned in muffled approval of his boldness as his head pushed between her lips and pressed onto her tongue, and she sucked on him, fitting in more of his length and pulling back and forth with her lips suctioned tight around his girth. He moved his hips back and forth in her face, holding her black hair in his hands and gently fucking her mouth. She gurgled with pleasure: this was a woman who was clearly more used to men who tried and failed to please her than men who succeeded.

He lifted up Julie’s tank top, cool and sandy from the dried seawater, and grabbed her tits eagerly, feeling them up and playing with her nipples. Julie kept sucking, moaning deep in her throat as she massaged Nathan’s cock with her lips and tongue. Her feet swayed back and forth as she enjoyed herself, and Nathan reach out past her head to grab her ass through her black bikini. He gave her cheeks a shake and a little smack, and felt Julie’s chuckle vibrate through his cock.

She kept on sucking, and he pushed his fingers under the bikini bottom to touch her bare ass, running his fingertips across her ass cheeks and between them along her crack. She arched her back, pushing her ass up against his hand, sliding her mouth up his length and pulling on his head with her lips as she looked up at him with her smokey blue eyes, her eyeliner smeared sensuously across her lids by her recent swim. Nathan looked back down at her; his mouth was hanging open and his breath was catching as she held his foreskin down and massaged his bare pink head with her lips and tongue, holding his shaft in her tight grip and staring up at him with that intense gaze of hers. Nathan moaned, and a squeak escaped. Julie raised her eyebrows at him playfully, and he came hard into her mouth, releasing his load and watching her swallow it down easily as it came, jet after jet, with her eyes closing in relish.

She popped his cock out of her mouth and smirked up at him.

“You’re not done already, are you?” she asked him.

“Hell no, I’ll cum again wherever you want me to.”

“That’s what I wanna hear.”

She stood up, brushing the sand off of her damp body, and Nathan stood with her, slipping his cock back into his trunks and putting his backpack on. She tied back her hair with the scrunchie on her wrist, and reached out to grab Nathan’s hand.

“Are we going to your place?” he asked.

“We are indeed. A cock like yours needs to get paid.”

Nathan grinned as she led him up an embankment and along the sidewalk down the beachside road, leaving the shore behind. His half-mast cock was wagging visibly as he walked, but there were few enough people out on foot that Julie wasn’t concerned, and she certainly wasn’t worried about people driving by paying too much attention.

Her house was less than half a mile away: a small but very nice beach house that had been made quite the mess of from a few day’s vacation.

Julie checked the microwave above the kitchenette.

“I’ve got you for about four hours, then I need you to leave,” she said brusquely, walking further into the house and picking up her purse lying on the couch.

“Okay. Someone coming over?”

“My husband.”

“Oh!”

“I owe you twenty bucks for sucking your dick, correct?” she asked, fishing through her purse.

“Yeah.”

“And the thirty you mentioned for sex, will that cover you until my husband gets back?”

“Uh, sure, yeah.”

“Good,” she said, handing Nathan fifty bucks cash and pulling her tank top off, revealing her perfect breasts (Nathan eyeballed them as 34C).

He stashed the money away into his backpack and dropped it onto the floor as Julie approached him, breasts on full display, putting her hands on his chest and gently pushing him around the sofa in front of a TV. Warm coastal sunlight poured in through the large wall-sized windows facing the sea.

“How old are you again?” she asked him. Her smoky eyes were interrogating him as much as her voice was.

“Thirteen.”

“Thirteen, wow.” She gave him a little shove and he dropped onto the sofa, his full erection standing in his strained swim trunks.

“You know, I’ve always fantasized about fucking a teenage boy,” she continued, pulling down her black bikini panties and standing before him in the nude, a tiny black bush peeking from the crook between her legs. “But none of them ever looked the way I fantasized about... until now. Now take your bathing suit off, I didn’t pay you to cover up.”

Nathan whipped his trunks off dutifully, sitting there naked in front of her, his hard cock standing straight up for ten inches. Julie sank to her knees between his legs and gave him another blowjob.

“I’ve never fucked a manwhore before,” she said thoughtfully, popping his cock out of her mouth and rubbing him up and down with some amusement. “Probably because guys are too busy trying to throw money at me.” She gave his head a kiss. “I haven’t paid for a drink in years.”

“Is your husband any good?” Nathan asked, fondling Julie’s tits as she sucked on him.

“Meh, he’s fine,” she responded apathetically, jerking him off. Her own saliva was slick under her grip. “You’re not being a homewrecker if that’s what you’re thinking. I’m only here for the rest of the week.”

She gave his cock a thoughtful look. “You have condoms in that bag of yours?”

“No.”

Julie looked up at him with some surprise. “You just rawdog all the women you hook up with?”

“Yeah, condoms suck.”

“Hmm.”

She took another meaningful look at his cock in her hands, then stood up.

“Fuck it, if I get pregnant I’ll just tell my husband it’s his.” She sat down next to him on the couch, legs wide open. “Now get in.”

Nathan leapt to his feet, grabbing her thigh in one hand and his cock in the other, holding it steady as he sank it into her, inch after inch pushing easily into her soaking entrance. Julie’s narrow gaze burst open into wide eyes as Nathan leaned over her, his swirling bangs hanging in his eyes, and grabbed her hips and began plowing as deep and hard as he could.

Julie seized his shoulders, her pink little mouth open in a perfect O, as Nathan swung his hips up and down into her, sliding his whole length in and out. Julie’s tight walls pushed and rubbed on his length, and her juices ran out whenever he drew his shaft out only to shove it fully back in.

He set his feet and bent his knees, giving himself more leverage to pump himself into her faster and deeper, thrusting his hips, feeling her vagina glide back and forth around his girth. He pounded her tirelessly, his full length disappearing and reappearing almost to the head as he pumped himself in and out, pushing her back onto the couch so he could let go of her legs and grab her tits, squeezing them in his hands as he rocked his hips forward and fucked her deep and fast.

Julie reached up and pushed his shaggy hair back out of his eyes, staring at his handsome face as he fucked her, and Nathan was more than happy to stare back: she was absolutely stunning. He squeezed and rubbed her full tits in his hands as he pumped into her, feeling her hard nipples against his palms, but when his load began pushing its way up, he let go, and supported himself on his fists anchored on the couch on either side of Julie’s hips, leaning over her body and pounding her with his full length.

“Are you gonna cum?” she asked him breathlessly. Her pretty face and chest were glazed with sweat, and her pale, sharp cheeks had become rosy.

“Yeah…” Nathan grunted quickly, focused entirely on her as he got closer and closer.

“Yeah?” She wrapped her legs tightly around his waist, trapping him inside her. He wasn’t planning on pulling out, but now he had no choice as he came hard, all ten inches pinned inside Julie’s pussy. Her eyes squeezed tight and her teeth were bared as she felt him empty his load into her, and heard him cry out as every rope he shot sent a jolt of pleasure through his entire body to his brain.

“Mmm…” She bit her lip, opening her eyes and looking up at him with satisfaction. Nathan, out of breath, face flushed, hair smeared in a mess across his forehead, looked no less dashing than he ever had. She let go of him with her legs, and he slowly drew himself out, still rock-hard.

“Good boy,” she assured him, sitting up and leaning forward to taste her juices on his cock. Nathan stood still, recovering as Julie licked and sucked on him, his cock still so stiff that it curved up past her face, wobbling and waving about as she pressed her tongue and face onto it.

“I know you’re thirteen and all,” she remarked, grabbing his shaft and looking up at it as it stood towering in front of her. “But this is special.”

She laid down on the couch, resting her head back against the cushions on the far end.

“Come here,” she ordered, wagging her finger at him and opening her legs. He jumped right back in, lying on top of her and pushing his cock inside her again as she wrapped her arms and legs around him and held him tight. Her tits pressed onto his chest and their naked bodies interlocked. He moved back and forth inside her, gentler and slower now, enjoying the feeling of her body. She rested her head back, closing her eyes again, with a small, contented smile on her beautiful face. He stared at her as he slid in and out, looking at the statuesque shape of her face and jaw, her sensuous eyes under their heavy lids, the smart arch of her eyebrows and the delicate inward curve of her nose. He looked at her bright pink lips, sweet and pouty, and on a whim leaned into her face to kiss her. She kissed back, chuckling deep in her throat as their mouths rested comfortably on each other’s. He moved aside a bit, giving himself room to put one of his hands back on her breast, holding it as he rubbed her hard nipple under his finger and thumb.

“Hmm, you like my boobs?” she muttered to him, completely relaxed.

“I love them,” he responded. His body rubbed onto hers as he humped her gently.

“Heh, I bet you do. Horny thirteen-year-old boy who doesn’t like tits? Pfft.” She made a small, dismissive wave with her hand.

She opened her eyes and looked back at him. “But only you get to play with them. Hmm? How does that make you feel, baby?”

“Hard.”

“Hard?”

“Yeah.” He began moving a bit faster inside her.

“Yeah? Are my tits keeping you horny?”

“Yeah!” He let go of them, anchoring his hands on the couch and starting to thrust.

“Get behind me baby, you can keep holding them!”

She rolled over onto her side, and Nathan slid in behind her on the couch, spooning her with his cock pressed against her ass. She reached between her legs, guiding him back to her pussy, and he reached under her arms, grabbing her tits again and continuing to thrust, his long shaft easily extending under her ass and between her legs into her.

“Ugh, that’s perfect,” she groaned, pushing herself back into Nathan’s body, clamping her hands on top of his as he held her tits from behind. He rested his head on her shoulder, their faces nestled into each other’s, and he pumped his hips up into her, his cock gliding rapidly in and out of her wetness.

“Yeah, you cum inside that pussy again, baby!” she grunted, as Nathan’s hot clean breath began to quicken against her face. “You let it all out!”

“Oh fuck, Julie…!”

“Do it, baby!”

“OH!” Nathan came again, squeezing Julie’s tits, pulling her body tight into his. His cock sat and soaked in her cunt as he emptied himself into her, and he suddenly relaxed, catching his breath and leaning on her. She rubbed his arms as he held her from behind, and the couple dozed off like that for a while, until they were both awoken by the jangling of keys at the front door.

“Shit!” Julie suddenly cried, bursting awake. “Nathan, get the fuck out of here!”

“Wha…” Nathan blinked, not quite sure where he was at the moment, but Julie was already on her feet and grabbing her scant clothes in a panic. A man’s voice rumbled from the other side of the house, and Nathan’s blood froze.

“Honey, what’s going on?”

“It’s um, I…”

Nathan grabbed his trunks, but the man appeared in the hallway across from him as he dove into the dining room next to the kitchenette and pulled them on.

“WHO THE FUCK IS THAT?!” he heard rattling with only a wall between them. “YOU FUCKING BITCH, DID YOU--”

“Listen, it’s not, it’s--”

There was a shocking smack: he had hit her. In that moment, everything fell apart.

“He broke in and tried to fucking rape me!” Julie cried suddenly, and Nathan’s blood somehow got even colder. He dashed around to the kitchenette as the specter of Julie’s husband crashed into the dining room, then from there Nathan dove back through the door he had been led in through. All of his money was left behind as he leapt into the sand under the deck.

“Julie, get the fucking gun!” the husband yelled from above, still sounding quite annoyed at his wife despite her alarming claims.

Nathan crawled around the perimeter of the house, peeking in through one of the large full-wall windows: she saw Julie rummaging through his backpack, pulling out all of his cash. That was almost a hundred dollars he had collected: gone.

Well, not if he could help it. He saw, as if watching a film, the husband enter the room from the right and bitch at her in a muffled voice through the glass. Julie dropped the cash back in the bag and rushed off, leaving it sitting abandoned on the sofa.

Nathan set his jaw. Setting back out into the city with no money again was about as dangerous as facing a man with a gun, he figured. He saw images of himself huddled under a bridge, wet and dirty, and he went back around the house to the front door the husband had used.

“Is he still out there?”

“He probably ran away! Let’s call the cops and just--”

“Fuck that, he tried to rape you, I’m going to shoot him. Give it to me.”

They both headed to the other side of the house, where Nathan had left. He crept back in, and the little house’s master bedroom was to his left. He glanced in: sitting there, on the nightstand, was a handsome leather wallet. He darted in, grabbed it, and slinked out through the front door again, only to hear the husband’s booming threats making their way around the property as he circled the house.

Wallet gripped in a sweaty hand, Nathan circled it with him, keeping his distance, until he reached the side door, and saw his backpack through the open doorway. He tiptoed back in yet again, grabbing his bag and slinging it over his shoulder as he bisected the house and headed to the front door again.

As he passed by, he looked into the guest room and locked eyes with Julie, who was in the middle of a police call. Her eyes, so beautiful and smoldering, were now wide with various kinds of terror and neither of them moved.

“...no,” she eventually said to the phone. “He’s not here. He was about… in his forties.”

Nathan gave her the finger before he made his final escape back onto the beach, dropping the wallet into his backpack and running literally for his life down the sidewalk, into town.

He didn’t stop running until traffic and pedestrians physically forced him to slow down: flushed, sweating, his wild hair askew and his feet sore, he dropped onto a bench and took a look at the wallet he had snagged. There was a hefty lump of cash in it: he went on to look for any credit cards.

“Harold Voss,” Nathan muttered to himself, looking at the man’s driver’s license. “Piece of shit.” 

Past the license was what looked like a dozen different cards, for insurance, roadside assistance, a gym membership, store credit… Nathan pulled the cash out and tossed the rest of the wallet into the trash.

Ninety-four bucks.

These rich-ass beach vacationers had ninety-four dollars in their wallet. Nathan was now carrying $184.25 in cold hard cash.

He looked up, at the people passing him by, countless random shapes on their own casual business, all with an air of assumption that the others around them had the same sense of purpose and the same capacity to do whatever they had planned to do. Suddenly he felt like one of them.

Suddenly he felt like a citizen of Bay City, California, making his way through life, riding its ups and weathering its downs, all with the rest of them. Two hot women strolled by, walking together, with bouncy hair, careful makeup, and revealing outfits with exposed abs, bare legs, and poking nipples. They both glanced at him as he walked by: he grinned confidently, and they shared a dainty giggle in response, one of them blowing him a kiss as they went on their way.

Nathan stood up from the bench and took a deep breath.

He could do this.


	3. Meredith

**Summary for the Chapter:**

> It's pretty easy for a teenage boy to sneak into a public gym. It's a bit harder for that same teen to slip into the lady's locker room and hook up with the hottest women he can find. But that's exactly what happens when Nathan meets the impeccably sculpted 42-year-old goddess Meredith Potter, who helps the young stud set up shop in a female changing room!

On a new day self-sustaining in Bay City, Nathan ventured away from the beach district, deeper into the heavier, more business-driven parts of the city than ever before. The streets were packed with people, and although this made it difficult to find women who he could get a private moment with, it he was seeing potential tricks everywhere he looked. It may have been a buffet, but he still had to play for his supper.

One place he had noticed a lot of beautiful women at was, unsurprisingly, the gym. Once he made sure that it wasn’t the same gym as the membership of the man whose wallet he stole and whose wife he creampied, Nathan loitered around outside the building for a short while, checking out the women who were going in. There were plenty of smoking-hot college girls, but there were also a bunch of gorgeous older women, all fit as a brick and perfectly coiffed, looking rich even in their sports bras and leggings, with toned arms and muscular abs all on display. Nathan had found his next workplace.

It was almost seven o'clock in the evening when he finally ventured into the gym. He was rested, fed, washed, and bristling with power. And he was horny as hell and ready to work. Not only had he slept in a bed at a motel (luckily the half-asleep concierge didn’t seem to care about his age), but recently he had also purchased some new clothes: a nice solid v-neck t-shirt and a fresh pair of shorts.

On the evening he finally went in, the first thing that hit him was a wall of freezing cold air. The second thing that hit him was the size of the place: high ceilings like a warehouse, stretching out far across to the opposite wall, with a plain of machines in between. The hum of the air conditioning, the neutral buzz of music being played over the intercom, the bustle of people moving about, the clangs of weights and the whir of the treadmills. The smell of sweat and antiseptic was everywhere. In front of him was a service desk with an employee who would make sure if he was a member or not. He wasn’t.

“I’m just here to see my mom,” he lied gracefully, pointing vaguely out into the array of machines. “Can I go in?”

The person at the desk waved him by apathetically, and he was set!

He ventured in, bike machines on one side and leg machines on the other, casually looking about. It was absolutely hopping right now, as the sun had just finished dropping behind the sea line and all of those hot rich-looking women were busying themselves with their post-job workout. In the forefront of the building, almost every treadmill and elliptical was occupied, and further back, the exercise racks and free weight areas were teeming with people. This seemed to be the time of night preferred by the more serious fitness enthusiasts, who were unphased by their recent shifts and still bristling with disciplined energy even towards the end of the day.

Nathan strolled through the gym, scanning everyone around him. There were plenty of potential prospects, for sure, but even though he had never actually been inside of a real public gym before, he knew that approaching a woman during her workout was about as taboo as talking to a woman with earphones in... and of course, many of them were _both_. Rows of mounted TV screens shone silently from the ceiling, and the intercom was blaring generic pop music. Only the percussion really survived the continuous cacophony of the machines and clanging weights throughout the giant room.

He frowned to himself, thinking with his hands on his hips. Suddenly a grunt snapped him out of his stupor as a man walked by him: Nathan had been standing in the middle of a walkway between two rows of equipment. He moved over to the wall, and saw that several yards down was a doorway leading to the men's locker room. Several more feet beyond this, past a water fountain in between, was the women's locker room.

Nathan blinked, and headed to the second door as if in a daze. He saw a woman in front of him head into the locker room: she was fit and pretty with her light brown hair in a ponytail and her gym outfit hugging her figure. Who knew how many other women were beyond that door? He was certainly not allowed in... but then again, he was also only thirteen. He would probably be forgiven.

Walking uninterrupted, he reached the door before he had a chance to weight his options, and boldly burst into the female changing room.

It seemed as busy as the gym itself, packed with all kinds of women in various states of undress. The air was thick with white water vapor drifting from carelessly running showers; amid the echoing din of countless cramped voices was the squeaking of feet on wet tiles; the whole place felt heavy with moist heat. Through the door was a short passage for privacy, that turned sharply and opened into rows of lockers on the right and showers and toilets on the left. There must have been thirty women in the place at once, and the moment Nathan made that turn and emerged into the changing area, he was noticed.

" _Hello_ , what have we here?!"

"Looks like someone got a package delivered!"

"Are you here to give me a workout, honey?"

"Who ordered the protein shake?!"

The reaction was almost overwhelming, whistles and cheers echoing chaotically around the tinny locker room. Nathan grinned, feeling every single eye on him as the women all dropped what they were doing to look as he walked into the changing area into their midst. He felt hands darting out from the crowd as he approached one of the locker aisles: they rubbed his shoulders, grabbed his biceps, plastered their hands across his hard chest and stomach as he went by, absorbing all of the attention around him.

"Oh he's _young_ \--"

"Did you feel his arms?"

"That's not all I wanna feel--"

He felt another hand pawing at his groin, but he kept walking, gathering women's gazes like a dragnet as he moved. An erection was beginning to grow in his shorts, but at that point, his flaccid penis was mostly just growing heavier and denser. He had developed a noticeable bulge when he turned a corner into one of the locker aisles... and found himself face-to-face with the prettiest woman so far, who stood firm in his path, fists balled on her hips, looking down at him with a stern but playful expression. Her nipples poked through her red sports bra, her bronze skin rippled on top of her lean muscles and tight abs, and her black yoga pants formed snugly around her toned thighs and hard-earned ass. She wore a blue baseball cap with a dirty-blonde ponytail hanging out the back and looked like she was into her forties.

"Well who are you, young man?" she asked him inquisitively, and the clamor in the locker room lessened somewhat as her sharp voice rose above many of the others.

"I'm Nathan."

"I'm Meredith, sweetie. So what are you doing here? Don't you know this is the women's locker room?"

"I do," Nathan answered quickly. "Which is why I came here looking for women!"

A huge cheer of approval erupted from the other women watching, but Meredith merely grinned at him.

"Oh yeah?" she challenged. "Well what do you have to offer?"

Nathan raised his eyebrow slyly, unzipped his shorts, and pulled out his penis for all of the women to see. It stiffened immediately under all of their gazes, and the cheering was deafening in the small room. Who knew what the men out in the gym were thinking of the noise? And more to the point, who cared?

Meredith drank in his full ten-inch erection with a melting expression, and she nodded.

"Looking to get that weapon wet, stud?" she growled, lurching forward and grabbing his cock with an almost painful aggression. Nathan flinched from her grip, and he felt half a dozen other hands suddenly swarm all over his body.

"Y-yeah," Nathan answered, clearing his throat and steadying himself as his shirt was pulled off messily over his head, pressing into his face as one of the women yanked it off of him. Instantly, he felt countless fingers tracing his young muscles all over his torso, and lips and tongues pushing and rubbing themselves against his bare skin. He had no idea who was doing what to him except for Meredith, who was hunched over, squeezing the head of his penis in her hands, her biceps flexing as she jacked him off. A pale woman with jet-black hair pulled his shorts off, leaving him fully naked as he kicked off his shoes; a thin blonde lady grabbed at his chest; a short, fit Latina rubbed his abs and then pressed her face on him, licking his flat stomach.

"Wait... wait...!" But Nathan's protest was drowned out as he was pulled down onto one of the benches that ran parallel to the locker aisle and pushed onto his back. They were supposed to be paying him! Almost all of his money was being sunk into nightly motel rooms--he couldn't afford to do this for free!

"I need--MMPH!" Someone pressed their lips onto his as Meredith pulled his cock into her mouth and began to suck. He felt long nails raking along his arm and the cold bench pressing against his bare back. Soft hands grabbed at his bottom, prying his cheeks apart, and he felt fingers pressing against his anus. Whoever was kissing him stuck their tongue into his mouth, and Meredith stroked and sucked him with all of the experience a woman of her age and appearance would boast.

Nathan moaned into whoever was so forcibly kissing him--he only saw a blur of dark wavy hair cascading across his face--and Meredith's mouth and tongue were massaging his member so expertly that within moments he felt the pressures of an orgasm rising in his balls. With an almighty yank he pulled away from the kisser and yelled "I NEED MONEY!"

His cry rang shrilly among the hard surfaces of the locker room, and he felt Meredith's mouth leave his cock right as he reached the point of no return.

"You want money, baby?" Meredith asked loudly, and the women all cheered again. She was jerking him off, fast and hard, finishing him.

"LET'S GIVE HIM SOME CASH, LADIES!" she cried as Nathan exploded with cum, his load shooting straight up into the air like bright white fireworks, splattering across Meredith's face and various other women who were crowded around him. He pumped thick ropes out and they jetted across the metal locker doors if they didn't hit someone first.

He looked around, breathing hard: an athletic college-aged girl with a purple headband, flushed in her face, was rubbing and kissing his chest with a heavy dollop of semen resting across her forehead and chin, while a heavily freckled woman with olive skin seemed to have been the one tonguing him. A big girl with curly hair and tattoos across her arms had a vice grip on his wrist and a glob of cum stuck to her hand.

"All right!" Meredith cheered, rolling her yoga pants off and straddling Nathan on the locker room bench. Her thighs were brown and muscular on either side of her shaved vagina, and she was hot and wet as she dropped herself down onto him and began to bounce on his length, which she fit into herself easily.

" _FUCK HIM, FUCK HIM, FUCK HIM_ _!_ " the other women chanted as they pushed their hands onto Nathan's chest and shoulders, pinning him down as Meredith worked her strong legs to ride on him. Nathan looked up helplessly to see a petite woman in her thirties with light brown hair and a smooth round face jeer at him as she reached above the others and tossed a five-dollar bill onto Nathan's flushed, heaving body. Others followed suit, and the floor became littered with soggy cash. Meredith took one of the bills and stuck it to Nathan's sweat-soaked face, leaning on her hands resting on his abs as she worked her ass up and down on his cock.

"Did my sweet baby boy bite off more than he could chew?" she taunted him, pushing his cock balls-deep into her, filling her mature body with his entire size. She leaned hard over him and pounded herself down on his cock as money continued to drift through the air around them. Right above his head, a cute plump woman in her twenties with thick-rimmed glasses and frizzy hair pulled down her own leggings and panties and sat right on his face. Other women held her hands for stability as she grinded her pussy lips right onto Nathan's mouth. Her thick thighs and strong smell almost overwhelmed him and he barely had a chance to breathe as his tongue was pinned sloppily against her roving labia. She came quickly and stood back up, but Nathan only had time to take a single gasping breath before yet another woman bent over and jammed her mouth onto his. He felt another hand groping his balls as Meredith pounded him, and he came hard inside of her, his groans muffled by whoever was sucking on his tongue.

The kisser pulled away, and even as Nathan looked down, Meredith was pulling herself off of him while another woman, a tall, lanky brunette with pale skin and long arms, dove down and stuffed his cock into her mouth. Meredith smirked down at him as he looked at her with wide, helpless eyes, and she plucked another bill from her purse, tossing it playfully into the air over him.

Nathan wiped sweat out of his eyes and swallowed, maintaining his composure as the pale, gawky lady sucked his dick enthusiastically. He was covered in welts and scratches, and his lips felt sore from being mashed against his teeth, but he was still as hard as a rock, and his balls were still tingling.

"You want more money, handsome?" asked a small, slim woman with a tight ponytail and dark, shadowy eyes, wearing a camo exercise shirt. She flaunted a twenty-dollar bill at him, and pulled her pants down. The tall lady let go of his cock, and an array of hands all lifted him to his feet as the woman with the dark eyes straddled the bench and bent over for him. Meredith got behind him and pushed him forward: he grabbed the woman's hips and stuck his cock inside of her.

A couple more bills drifted through the air as he pounded her, and he was kissed yet again by a broad-faced redhead. The slim woman's pussy was tight and soaked, and with all the other women feeling him up and cheering him on, he came after just a short while and was presented with still another paying customer, who stripped, laid on her back on the bench, and spread her legs for him. He positioned himself over her, pushed his cock inside, and kept on thrusting.

By the time the money stopped, the floor was covered in a messy carpet of damp bills, and a few were even stuck to his sweaty skin as he pounded down into his current trick, his hands gripping her round breasts, swarmed by other women.

"Oh fuck..." Nathan moaned as his next load rose up in his balls. "Oh my god..."

He came inside the woman with the round breasts, who gushed on his penis and was pulled away and replaced by a platinum blonde with a heavy tan, who sat on the bench in front of him and sucked his cock hungrily.

"Anybody got any water?" he asked loudly with one hand resting on the blonde's head bobbing at his crotch, and was immediately presented with a dozen different water bottles. He chugged his fill, rehydrating himself after having been drained dry from repeated orgasms, and by the time the platinum blonde had finished sucking, he was ready to go again. He sat down on the bench, and a dark, muscular woman climbed on top of him and rode his dick, while another woman handed him a bottle of Gatorade. The sugary drink rejuvenated him, and he tossed the empty bottle aside and grabbed the muscular woman's hips, guiding her as she thrust herself on him, her taut, firm breasts hovering exposed in front of his face, hard nipples brushing his mouth. He sucked on them, and grabbed her ass, letting his cum shoot freely inside her as she bounced on him.

Nathan collapsed back onto the bench, gasping for air, his cock at half-mast lying across his abs, completely drenched. The women all applauded him as they finished getting dressed, and Meredith herself pulled her pants back on.

"Looks like I have to take back what I said before," she remarked, watching as Nathan sat back up and began collecting the numerous bills scattered around the floor.

"What's that?" he asked, regarding the money skeptically: there were plenty of ones and fives, several tens, and even a few twenties, but they were all dripping with shower water.

"I said you bit off more than you could chew," she reminded him, handing him his shorts. "Well, I take it back."

"Thanks," Nathan remarked. He got dressed in front of her, but she continued to watch him with a considerable amount of interest.

"I have a proposition for you, Nathan," she said finally as he pulled on his shirt.

"A what?"

"I'd like to take you home and cook you dinner."

Nathan looked at her. "You want to cook me dinner?"

"And after dinner, I want to make love to you in my bed. Just the two of us. I'll pay you again."

"Oh!" Nathan grinned, pushing his sopping wet hair out of his eyes. "Yeah, that sounds nice. I am pretty hungry."

Meredith smiled, outwardly warm but clearly still ravenous. "Oh I'm sure you are. Even if you hadn't blown five loads in a row, boys your age are always hungry." She winked at him, and offered him her hand. He took it, and they walked out of the lady's locker room boldly together, the few double takes they attracted overshadowed by far more gym patrons who simply didn't pay attention to them.

"So where do you live?" Meredith asked him as she drove them through the night of the city in her expensive Ford.

"This motel off of Lexington Street. It's pretty gross but it's the cheapest place around."

Meredith glanced at him. "You're living in a motel? Like on your own?"

"Yeah on my own. I ran away and I'm never going back."

"Wow. You, uh..." She glanced at him again. "You don't have a pimp or anything? How old are you?"

"Thirteen."

"Thir... huh." She nodded to herself, processing. "You know, it's not every boy who can live the way you do."

"Well I don't care about other boys."

Meredith burst into laughter. "Well why would you! You've clearly got plenty of girls to pay attention to!"

She pulled into the driveway of a townhouse in the middle of a quiet row on the outskirts of the city. The streets were much darker here, but also cleaner and wider, and of course quite a bit quieter.

"Nice," Nathan remarked as he followed Meredith out of the car and into her house.

"Thank you, yes this is my place," she said with a humorously dramatic gesture as she turned the lights on in her foyer and locked the door behind them, taking off her baseball cap and letting her dark golden hair loose in its large bouncing spirals. "You can go ahead and put your shoes on this rack..."

"You're single?"

"Been happily divorced for eight years, baby boy," she assured him, kissing him smartly on the lips. "But let me tell you, I know plenty of those girls who couldn't keep their hands off of you in that locker room, and I assure you, you turned plenty of proud men into cucks tonight."

Nathan shrugged coldly, and this seemed to excite Meredith even more. She seized his wrist.

"Listen baby, if I was still married to my piece of shit ex when we met, don't worry, I'd have fucked you either way."

"I know."

" _Mmm_ , men three times your age don't have a third of that confidence. Good fucking god."

She gave him another peck on the lips and headed further into the house, through her lavish living room into her resplendent chrome kitchen. The house had high ceilings and was tastefully lit and decorated, but it was also fairly small.

"So here's the plan tonight," she said, taking out a frying pan from a cabinet in her kitchen. "I'm gonna cook us something, then I'll go up and take a shower and we can get down to some more fun, okay?" She wiggled her ass in emphasis as he joined her in the kitchen.

"Want me to shower with you?"

"Oh no," she answered, setting a large saucepan on the stove. "I want you nice and sweaty." She looked over at him lustfully. "I'm a traditional gal. I think women should be clean and men should be dirty." She stuck her tongue out at him and opened her pantry. "So what kind of food do you like, Nathan?"

"Oh I try not to call the shots when someone offers to feed me," Nathan said. "But, uh... I'm just not very fond of meat or dairy stuff. If possible, you know."

Meredith pointed at him smartly. "I've got you covered, handsome." She stepped over to her fridge, then paused. "In more ways than one," she added with a wink.

Nathan smiled. He was mostly unaffected by Meredith's energy, which he secretly found quite overzealous, but that hardly meant he didn't find it very hot that her enthusiasm was directed exclusively at him. Meredith pulled a pack of vegan patties from deep within her freezer and cooked Nathan up a bean burger. He ate ravenously, and like Meredith had said, his recent exertions were only part of why he was so hungry. He had also spent the past week spreading deli subs across multiple meals. Meredith sat across from him with her own dinner, watching him eat with a look of maternal satisfaction.

"Must be tough living on your own," she said, taking a bite of her own sandwich.

Nathan nodded, slowing down and reaching for a napkin from the dispenser at the center of the kitchen table. "Yeah, most of my money goes into my motel room."

She leaned on one hand, gazing at him lovingly. "So how many... uh, _customers_ have you scored so far?"

Nathan swallowed his food and took a sip of water. "Just a few per day. That's usually enough to keep me going." He hunched over, tracing out his thoughts with his fingertip on the table. "Like I said, getting a room is always the most expensive part. Once I have that covered, the rest is always plenty for food. And recently I was able to afford some new clothes!"

"Well you won't have to worry about that for a while with all the money you got in that locker room! Plus, you are more than welcome to spend the night with me."

He grinned. "I just might take you up on that."

"I thought you would."

Meredith took up their dishes and placed them in her sink. "All right, you can follow me to my bedroom, and make yourself cozy while I wash up!"

Nathan followed her up her curving staircase and down a wide carpeted hall into her room. Her bed was wide and tall, flanked by sturdy wooden frames, and the bathroom door was directly ahead of it. Meredith pranced in and closed the door behind her as Nathan stripped naked and relaxed back against the bed's large lush pillows, his flaccid penis still six inches long and resting between his thighs, still covered with dried cum, spit, and juices from the various women in the locker room. It had been a while since he had slept in a good bed: those motels felt cozy after eighteen hours awake, but at that point any quiet surface would.

Nathan heard the shower turn on. He rested his head back and closed his eyes, anticipating what was to come. Meredith was fit, experienced, and tight, and she knew her way around a penis. It made Nathan excited, and he began to grow just waiting for her to emerge back from the bathroom. He fell asleep with a semi, and the time passed quickly until he woke up to the bathroom door opening again some time later.

Nathan was stunned. Meredith had carefully blow-dried and redone her bouncy golden-brown hair and reapplied her eyeliner and blush. She was fully naked, and her perky firm breasts poked forward from her hard, toned body, her tanned skin smooth and freshly shaved. Nathan instantly reached his full ten inches, and she approached the bed coyly.

"You're thirteen," she said as she crept closer. "I'm forty-two. A cute little boy like you needs a woman who knows how to treat him. Isn't that right?"

"Yes ma'am," Nathan said breathlessly, his stiff cock nearly lifting off of his abs as it rested up across his body.

Meredith grinned as she climbed slowly onto the bed, between his splayed-out legs, his cock right in front of her, with heavy balls churning fresh cum so powerfully it was almost visible to her. She pushed her wavy hair behind her ear, bowed her head, and gave his shaft a gentle little kiss. It quivered, and she grinned and kissed it again, planting little pecks all the way up his length. Her perky golden-brown breasts hung beneath her as she inched up his body, kissing him along the way, until she reached his mouth and brushed her lips onto his. He grabbed her hips and she laid on top of him, grinding her cunt on his cock and opening her mouth. Their tongues met, and they licked each other playfully; Meredith's breath smelled of recent minty mouthwash, but Nathan had only brushed his teeth before leaving his motel room that morning. She didn't seem to mind, though. His cock was throbbing against her clit. She had smeared juice all up and down its length with her humping, before she had even put it back into her.

They continued to lick each other's tongues, and soon Nathan's cock was so hard that he was grinding back up onto Meredith, and Meredith took this as her cue to finally bring him back inside her. She lifted herself off of his body, took his cock in her hand, and stuck it between her legs, lowering herself down onto its length as easily and smoothly as she had done back in the locker room at the gym.

"Oooohhhh..." Nathan groaned as Meredith pushed herself agonizingly slowly down his shaft. Meredith chuckled.

"Yeah, that's what that big cock has been waiting for, hasn't it?" she purred, and she pulled herself back up, gradually running her lips across his length, and then, just as slowly, pushed herself back down on him, holding onto his lean shoulders and resting her body down on his. He wrapped his arms around her and held her close as she moved gently and carefully up and down on him, pausing every time she felt him tremble or heard his breath catch. Her hard nipples raked his chest as she moved on him. It was quite the drastic change of pace from her chaotic aggression in the locker room.

"Oh my god," he gasped, his cock full to bursting inside of her.

"Mmm, never had pussy like this before, have you?" she teased him, her body sliding back and forth on his with an experienced, athletic grace. Nathan shook his head mutely, and Meredith gave him a sweet kiss on his cheek before moving back towards his mouth. Her face became serious, and she held his face in her hands, sucking on his lower lip as she rode him. Their kiss was just as slow and sensual as their fucking: Meredith could tell that, had she tried to speed things up with her tongue, Nathan probably would have lost control and started thrusting up into her. She certainly didn't want that. She was building the boy up so his sixth load of the day would be his biggest one yet, and she planned on enjoying every drop of it.

They kissed gently, sliding their lips across each other's, their little pecks separating with small smacking sounds. Nathan ran his hands down her bare back to her ass, holding her cheeks and squeezing them. She moved herself back and forth under his touch, feeling his member tremble inside of her.

Finally she lifted herself off of him and crept back down between his legs, holding the base of his cock and sliding her tongue along his shaft as she lay on her stomach at his crotch. But his cock was too large for her to reach the top while lying down, so she pushed herself up onto her knees, hunching over his length.

"Now I want you to just lie still, baby," she told him warmly. "I know you're getting paid for this but I still am going to do all the work." She pulled his foreskin back and sucked on his head.

"M-Meredith," he moaned. "I'm REALLY close."

"Whoops!" she teased, letting go of his cock entirely. It fell back against his abs, and she smirked at him.

"I'm going to pay you ten bucks for every rope you shoot," she told him. "So you better give me everything you've got!"

She picked his cock back up and continued to suck on it, but at last she was moving faster, squeezing him tight with both her mouth and her hands.

"Oh, oooooh..." Nathan reached out and grabbed her arm; her toned bicep flexed under his grip, and her wavy curls bounced as she moved her lips and hands up and down on his shaft.

"Mm-hmm?" Meredith moaned into his cock, and Nathan moaned right back at her. She pumped her arms up and down on him, sucking hard and bobbing her head, squelching noisily onto him.

"Yeah, keep going, keep going..." Nathan panted, and Meredith didn't miss a beat, working his cock faster than ever. Her wrists rotated perfectly and her tongue slid rapidly across the base of his head and his pee slit, making his legs tremble and his chest and face flush a bright red.

"Oh fuck... oh fuck, Meredith..."

"Yeah?" She moved her mouth off of him and jerked his load out. Her hands flew up and down his long shaft, and when he was finally about to cum, he batted them away and grabbed himself.

Semen exploded from his tip and drenched her face. She laughed out in victory as Nathan held his cock firmly and kept his foreskin back. Another burst of cum flew off to the side and splattered against the bedsheets. Twenty dollars. A third went over Meredith's head. Thirty dollars.

Meredith watched the fruits of her labor in awe. Thick white jets streamed repeatedly from his cock, some of them splashing across her firm breasts, some arcing backwards and landing on Nathan himself, some of them going straight up and sprinkling back down on both of them. By the time he finished, Nathan had shot nine full ropes of cum.

"Holy shit," Meredith breathed. "That was everything I thought it would be." She was covered in cum, licking it off her mouth as it ran down from her forehead and nose onto her chest, then leaned over Nathan and licked his own cum clean off his abs.

"Well I guess I owe you some money now, don't I?" She got up from the bed and went over to her purse, smacking down ninety dollars onto the top of her dresser drawer.

"That's for you, baby. Now, if you'll give me a moment, I have to clean up again."

She winked at him and headed back into the bathroom. This time, Nathan followed: as she was busy taking another shower, Nathan stayed at the sink, opening her drawers until he found her hair dryer. He counted his money from the locker room as he blow-dried it: even before Meredith had taken him home, he had made nearly two hundred dollars. _And_ he had a free dinner, and a free bed for the night.

Once Meredith came out of the shower again, he helped her change the bedsheets, and they fell asleep securely in each other's arms.


	4. Rebecca & Hosanna

**Summary for the Chapter:**

> What if they're gay, but you can't stay away? That's the dilemma Nathan is facing when he meets a hot lesbian couple: 24-year-old Rebecca Mooring, topless in a plain white bra, and 21-year-old Hosanna Stein, braless in a crop-tied tank top, neither of whom are particularly fond of random men who approach them for sex... or men in general.

The great South Cobblestone Plaza in Bay City, California was intimidating to thirteen-year-old Nathan Monroe, who had grown up largely in the suburbs. It's amber-colored glass panes reached up above his head as far as he could see, gleaming golden in the beachside sun, and the sophisticated landscaping of its courtyard, with two matching fountains and rows of immaculate shrubbery, made the place feel very adult indeed to the green young runaway. But he had to brave this opulent place: it was the home of the local branch of the Brownleaf National Bank, where he was hoping to deposit the considerable cash he had earned at the nearby gym. Besides, what did he have to fear of the adult world? He had already enjoyed some of the most adult experiences possible!

It was no less resplendent inside the plaza, with its shiny hard tiles and brass fixtures all around, but the actual bank itself was a welcome downgrade, softly carpeted and surrounded by mild robin's egg wallpaper. Still, its teller booths were high and surrounded with bulletproof glass: not exactly a nursery!

He stood in line for a few minutes; even though he felt very out of place surrounded by adults, he wasn't paid much mind. It really wasn't so out of the question to see a teenager running these kinds of errands, especially in a big city like Bay. He was put even further at ease when he saw how hot his teller was! She looked to be in her early thirties, dressed smartly in a traditional white work blouse and dark blazer, with her blonde hair tied up in a utilitarian bun, her pretty face soft and round, but also sharpened by professionalism. She saw Nathan approaching her and beamed, apparently just as delighted to see a handsome young man as he was to see a beautiful mature woman. Her customer service façade relaxed and she received him enthusiastically as he approached her station.

"Hello there, young man," she welcomed him brightly as he walked up to the kiosk. "How may I help you today?"

"Hello! Uh, can I create a bank account and deposit some cash into it?"

The teller looked at him a bit closer. "Have you ever opened a bank account before?"

"No, ma'am."

"Well young man, I have to let you know that if you're under eighteen, you do need to share ownership with a parent or guardian."

"Oh. Well then, yes, I'm eighteen."

The teller smiled and leaned forward on her desk, resting her head on her hand and looking at him dreamily through the glass pane. "Well that's good news," she teased. "So you got some cash you're looking to deposit?"

"Yep!" Nathan pulled the wad of money he had earned from the gym locker room and smacked it on the desk on his side of the glass. The teller perked up.

"Oh! How much is that?"

"Two hundred and ten dollars."

The teller slinked back down against her desk. "And how does an _eighteen-year-old adult_ earn such a sum?" she asked coyly.

"I provide personal services," Nathan answered, just as coyly, sliding the bundle of bills through the slit at the bottom of the glass pane. The teller touched his hand receiving it.

"Personal services?" she repeated, sounding genuinely interested.

"For women."

She inhaled deeply in surprise, swallowing a lump that spontaneously formed in her throat.

"Oh..."

She looked down at Nathan's cash.

"Do you... have a driver's license?"

"No ma'am."

"Do you have any kind of identification?"

"No ma'am. My name is Nathan Monroe and I currently live at the Minute Motel off of Lexington Street."

She blinked, staring at him, and then looked down at his cash. She took a breath.

"Well, Mr. Monroe, unfortunately I can't legally create a bank account in your name with the information you can provide." She looked up at him. "But I do really want to help you." She swallowed again, another lump in her throat. "If you can come back in about four days anywhere between noon and when we close, I'll be here and can tell you if I've managed to create a savings account for you." She raised her eyebrows at him, passing his cash back under the glass pane. "Is that okay?"

Nathan nodded, taking his money back. "So what you're telling me is you get off work when the building closes?"

The teller laughed. "Yes, that is true."

Nathan leaned closer to the glass. "Maybe I can meet you here and offer my services?"

The teller licked her lips nervously. "Yes, I think I would like that. I'll be in the courtyard tonight at ten.

"Good deal." Nathan winked at her and walked off, stowing his money back into his bag.

Even though he hadn't managed to make an account, he was still in fairly high spirits that day. He dropped his backpack off at his motel room and went off to a nearby gas station convenience store he had taken a liking to, looking for some snacks. It was currently not quite two in the afternoon: he still had plenty of time in the day, the sun was high in a clear blue sky, and even this deep into town, a warm current was carrying the salty smell of the sea. He was about to head into the convenience store when a car pulled up to one of the pumps and two girls got out.

The girl in the passenger seat seemed to be the older one: she was a tall, curvy young woman with wide hips, thick thighs, and full round breasts that hung heavy in her beige bra, which she wore openly without a shirt. Her legs stretched her tight booty shorts, the bottom of her smooth ass hanging out from under them, and an assortment of floral tattoos surrounded her thick torso like a belt which spilled over her waistline in a cute muffin top. She had a sweet wide face and big eyes behind a pair of large glasses, and her hair was light brown, hanging long and straight past her shoulders.

The girl who was driving was a couple years younger, and much more petite: she was short and thin, wearing a skimpy white tank top that hung carelessly off her skinny shoulders, and from the looks of it, there was no bra at all to cover her small firm nipples if she moved too far one way or the other in her loose top swinging back and forth. Like her girlfriend, she wore glasses, but hers were thick-rimmed and small, and her hair was jet black and tied into a messy bun behind her head and short-cut bangs up front. Her top was tied up into a crop knot high above her belly button, showing off her flat stomach above her tight black leggings, but her tattoos seemed to have been concentrated on her arms and shoulders. Her face was very pretty and heavily freckled around her nose which was graced with a septum piercing, but her expression was stern and she seemed to have a case of resting bitch face.

But what struck Nathan most of all was the light, fuzzy hair he saw on their legs and under their arms as they went about pumping their gas. He was intrigued, and felt drawn to both of them immediately.

They barely paid him a glance as he approached them across the gas station lot, largely ignoring him, only doing a brief double-take when they realized how young he was. The petite one was filling up the tank while her girlfriend stood by.

"Nice shirt," he said to the tall thick one, topless except for her bra.

She looked at him and laughed, a bit sardonically, but only a bit.

"Thanks," she said, while her girlfriend rolled her eyes with annoyed disinterest as she worked the pump.

"Yeah, I guess it's the only way to show your tattoos, huh?"

"I guess so," she said, looking down at the floral linework surrounding her belly. "You like them?" she asked, turning towards him.

"Yeah! They go all the way around your body?"

"Yeah!" She did a little spin for him.

"Hey, buddy," the other one interrupted, putting the gas pump away. "Can we do anything for you, or are you literally just hitting on my girlfriend?" Her voice was unimpressed and rather cold.

"Well now, I think he's okay," the tall one said, giving Nathan the familiar up-and-down look.

Her girlfriend took a look at him too, hers distant and more analytical.

"Yeah, he's okay for a guy," she admitted. "But you're also a fucking kid. Where's your mom?"

"Oh, I'm a runaway," Nathan explained brightly.

"WHAT?!" the tall one gasped, but the petite one seemed pleased.

"All right, man," she said with some degree of approval. "And what, you need a couple of mommies to take care of you?"

"Something like that."

"Well I for one am all for it," said the tall one, jokingly hopping up on the small concrete platform the gas pump was built on so she could bend over to talk to Nathan--who was otherwise her height--as if he was a small child. "Would you like to come with us to get some food?" she asked sweetly, her hands clamped between her bare thighs and her bra, slightly too loose, hanging off her breasts just enough for Nathan to see the edge of her areolas.

"I'm always down for eats!" Nathan answered, looking down at her swinging breasts.

" _Hey_ ," she said loudly, putting her hand on his chin and pushing his gaze back up to her face. "Eyes up here, buddy!"

"My bad," Nathan said softly, blushing a bit. But the girl just laughed and pulled her hand away.

"Nah, I'm just kidding, I don't care if you look."

Her girlfriend scoffed. "Rebecca! Don't say that!"

"Why not? They're just tits, I don't care if he sees them!" Rebecca looked from her girlfriend down to Nathan and pulled her bra up, flashing her bare breasts at him right there in the middle of the gas station parking lot. "There you go, kid," she said warmly, showing him her soft pale tits and wide nipples.

"Ugh, you are such a slut," her girlfriend groaned, getting back into the driver's seat.

"Oh please, you like him, too!" Rebecca called after her, pulling her bra back on. "Come on buddy, you can sit in the back with me," she told Nathan, opening the car door for him. Nathan eagerly climbed in, and soon all three of them were off.

"So where do you wanna eat?" Rebecca asked him, sliding her arm around his shoulders as they sat together.

"Uh, we're eating wherever _I_ want to take us," the slim girl protested from up front, pulling out of the gas station parking lot and turning on the stereo.

Rebecca rolled her eyes. "That's my girlfriend Hosanna," she explained. "Hey, what's your name?"

"Nathan."

"Nathan... well Nathan, I hate to tell you that Hosanna and I are as gay as the dinosaurs from _Jurassic Park_ , but you're okay in my book."

"Yeah, plus you're like ten fucking years old," Hosanna added, glancing back at them in the rear-view mirror.

"I'm thirteen!" Nathan protested.

"Oh yeah, fucking ancient, my mistake."

"Officially a teenager, last time I looked."

"Teenagers _are_ kids."

"You know if it were a hundred years ago I'd be fighting trench warfare in France right now."

"If it were a hundred years ago, _I_ _'d_ be married to some forty-year-old drunkard who just finished raping his sixth kid into me."

"She's got you there, buddy," Rebecca remarked, pulling him in close to her.

Hosanna turned a corner, and Britney Spears started playing on the stereo.

"Whooo, throwback time!" Rebecca laughed, and Hosanna cranked the volume up.

Rebecca bounced herself off of Nathan, sliding her wide ass across the car seat as she danced to the blaring music.

"Well, all right!" Nathan responded, sidling up next to her, and the two jammed together as Hosanna drove through town. Rebecca bit her lip, watching Nathan move about in his seat, and soon she moved herself over onto his lap.

"Louder, babe!" she called over the music, already blasting, and Hosanna laughed and rolled the windows down.

_"My loneliness is killing me... and IIIIII..."_

Rebecca began grinding on Nathan's lap, and he got instantly hard. Far from deterring her, she gave him a lapdance to the beat.

_"I must confess... I still belieeeve!"_

Rebecca sang along loudly as she humped Nathan's erection with her wide, firm ass, the city rolling by through the fully open windows.

"Get it, girl!" Hosanna cheered as she watched her girlfriend grind on Nathan through the rear-view mirror. They sang together: _"When I'm not with you I lose my miiiiind..."_

"This song must sound old as shit to you, huh?" Rebecca asked him, leaning over to open the console between the front seats and pulling out a pack of cigarettes. She had to yell to be heard over the music.

"What's wrong with that?" Nathan answered brightly, holding onto Rebecca's hips as she humped him.

"Hell yeah!" She lit her cigarette and took a deep pull. _"Boy you got me bliiinded..._ you smoke, Nathan?"

"I've had pot before."

"Not tobacco? Good for you. We got pot at our place. Don't smoke this shit. _Shoooow me, how you want it tooo beeee..."_ She danced on him good, planting her feet on the floor of the car and puffing on her cigarette as she rubbed her ass back and forth on his boner. Nathan lifted his hands and grabbed her full breasts through her bra from behind. Rebecca cheered.

Hosanna turned the music down as they pulled into a fast food drive-thru. "Cut that shit out guys, we're in public."

Rebecca slapped Nathan's hands off of her breasts and got off his lap as Hosanna began to order.

"You like partying, buddy?" she asked him softly, leaning close into him.

"I love to party! And I have rates, too."

"Ooh! Hell yeah, I'm down for that! Just wait til we have our food, you can tell us all about it, okay?"

She grabbed his hard standing tent through his shorts and gave it a brief squeeze before letting go and facing forward, putting her cigarette back into her mouth.

"What do you want, Nathan?"

"Uh, how about a veggie fajita?"

"And you, babe?"

"Make that two, hun."

Hosanna pulled back out into the road after she finished ordering, food in one hand and wheel in the other.

"Well Hosanna," Rebecca said as she ate with Nathan in the back. "It turns out Nathan has _rates_!"

"You mean like for sex work?"

"Yeah," Nathan answered. "I charge ten bucks for kissing and--"

"Hell yeah, that's awesome!" Hosanna exclaimed. "I approve!"

Rebecca turned towards Nathan, her mouth full of food. She smiled at him, and Nathan leaned into her, opening his mouth. Rebecca passed her chewed food to him like a mother bird, and Nathan swallowed it contentedly.

"We are a thousand percent supportive of sex workers," Hosanna assured him, threading recklessly through traffic while eating, and Rebecca nodded in agreement, pulling on her cigarette with her mouth still full of food.

"We'd be happy to bring you to our apartment and pay you," Rebecca said once she swallowed.

"Gay as the dinosaurs from _Jurassic Park_ , huh?" Nathan teased, leaning into Rebecca's shoulder.

"Looks like you found a way," Hosanna quipped back, and Rebecca ruffled his hair.

"Oh, I'm not against it," Nathan said. "Just making sure you guys are fully on board."

"Well that's very sweet of you," Rebecca said.

"And probably part of the reason why we'd make an exception for you," Hosanna added.

"Sometimes all it takes is literally the bare minimum," Rebecca agreed. "Like asking for permission."

"She's joking, it takes more than that for a lesbian to want a dick," Hosanna said, pulling into their apartment complex parking lot. It was a bit run down, with cracked pavement and faded walls, but Hosanna drove through it with a warm familiarity. "Kid's _got_ something, Rebecca, I can't really describe it."

"I think I can describe it," Rebecca said. "Long, hard, stiff..."

"Yeah, that's all well and good," Hosanna said, parking in front of their slightly sagging building. "But I'm more interested in what his tongue can do."

"Ten bucks and you can find out," Nathan said.

"Hell yeah, kid," Hosanna responded as they all got out of the car and headed into the apartment. The walls were decked with all manner of colorful art prints, and the coffee table--in between a medium-sized TV standing on the floor and a large, cushy sofa strewn with blankets--was covered in messy papers and a couple of empty bottles.

"Sorry about the mess," Hosanna muttered, but Rebecca had already locked the door behind them and led Nathan by the hand into the room, scooping him up in her arms and kissing him deeply.

"Want me to set up the bong, babe?" Hosanna asked, walking past the kissing couple and into the equally messy bedroom beyond.

"Mm-hmm..." Rebecca moaned into Nathan's mouth. They held each other tight, rubbing tongues, and Nathan felt Rebecca's soft, naked back with his splayed-open hands. His stiff cock rubbed onto her, and she pushed back onto it as Hosanna returned with the bong, clearing the table off for it and stepping into the kitchen to grab some ice cubes. She had let her hair down: it tumbled black as coal to her shoulders, framing her face closely on either side of her severely cut bangs. Her nipples were poking clearly through her tank top as she loaded the ice into the bong.

"C'mon, gimme," Hosanna moaned playfully, grabbing Nathan's arm and pulling him away for her own turn. Nathan spun around and flung his arms around Hosanna instantly, pushing his cock against her thinner body next, and Hosanna stuck her tongue out to meet his as they began kissing.

"That boy kisses like a forty-year-old dyke," Rebecca said as she sat on the sofa and prepared the bowl. Nathan's wondering hands pulled at Hosanna's tank top, unraveling her crop knot and causing the fabric to drop down and cover her flat belly. Hosanna pulled the shirt off over her head and dropped it on the floor; Nathan's touch instantly slid across her ribs to her perky pink nipples, which he rubbed with his fingertips.

Hosanna broke away. "We need some fucking music!" she cried, stepping away and going over to the TV, casually topless. "Rebecca, take care of him."

"I'm doing this!" Rebecca shot back, still packing the bud in. "Here, he can look at my tits some more." She whisked her bra off and tossed it on the floor with Hosanna's tank top. Her breasts were much wider and rounder than her girlfriend's, with flatter, paler nipples.

"I think we should make this a Britney kind of hookup," Hosanna said, as Spears once again loudly filled their space. Nathan hopped onto the bouncy sofa next to Rebecca, who planted a kiss on his cheek and grabbed his wrist, pulling his hand onto her tit. He squeezed and held her breast as she lit the bowl and took a hit. But while she needed a moment to recover from the massive plume of white smoke she blew out and the coughing fit that followed, Hosanna had already pulled her leggings and panties off, and stepped up onto the sofa, standing naked on its cushions, her hairy vulva almost directly at Nathan's eye level.

"Come here, boy," Hosanna growled, grabbing Nathan's dark locks and pulling his face fiercely into her crotch. Nathan's hand was yanked off of Rebecca's boob and smacked onto Hosanna's thigh as he tried in vain, his protests muffled against Hosanna's long pubes, to pull away for air. But Hosanna had different plans. She grinded her crotch onto Nathan's face, rubbing her clit onto his lips and tongue, which were smashed against her vagina, smearing spit. Her smell was intense, and when Nathan did manage to take a breath, that seemed to be all that entered his nostrils.

"Oh hell yeah," Rebecca exclaimed, putting the bong down and standing up to take off her own shorts and panties as Hosanna whooped loudly, pinning Nathan's face into her as he squirmed about between her legs, waving her other hand in the air and singing along to the music blasting from the TV on the floor.

" _But to lose, aaaaall myyyy seeeeenses..._ whoo babe, take it _off_!"

Rebecca finished stripping naked and went over to kiss her girlfriend as she humped Nathan's face.

_"Oh baby, baby...!"_

Nathan had managed to free his nose and find a stream of air, and was then able to push his tongue out fully so Hosanna could properly rub her clit on it. He looked up, far above him it seemed, to see Rebecca and Hosanna kissing passionately, their tongues locked together.

Then Rebecca turned around, sticking her ass against the side of Nathan's head, and Hosanna finally released him... only for Rebecca to grab him next and pull his face into her ass crack. But this time he was ready, and had his tongue out to meet her.

Rebecca whooped and twerked onto his face, not too differently from the lap dance she had given him in the car... and still loudly singing Britney Spears.

_"You see my problem is clear-- I'm dreaming awaaaaay..."_

"Mm, fuck!" Hosanna moaned, watching her girlfriend's ass rub onto Nathan's face. "He looks better with you, babe."

"Oh please, he looks better with _you_."

"You can't even see him!"

"I--"

Rebecca turned to look over her shoulder, reaching back to grab her ass cheeks and spread them. Nathan licked her butthole as fast and steady as he could, his jaw beginning to feel sore.

"His tongue, huh?" she said, as Hosanna nodded, masturbating vigorously.

"Oh fuck bring him back!"

Rebecca let go of him and Hosanna pulled his face into her crotch again as she exploded in an orgasm and squirted directly into his face. Nathan squeezed his eyes shut as he felt her smelly juices spray onto his face and into his open mouth, against his outstretched tongue.

"Holy shit," Rebecca muttered, bending over instantly to lick her girlfriend's ejaculate off of Nathan's tongue and lips. She held his wet face in her hands, her breasts dangling under her as she hunched to kiss him, but the girls weren't done with his face yet. They pushed him back onto the sofa and straddled him together, their asses rubbing onto each other and against his face, soaking pussies pushed up against his sore tongue.

Nathan's penis, meanwhile, was tearing against the confines of his shorts. When he blindly pulled down his zipper to release the tension of his full ten-inch erection, the lesbian couple sitting on his face didn't even notice at first. But Nathan still felt relieved, and his throbbing cock stood freely out in the air as he reached up and grabbed at the two asses roving around on his face. Rebecca came, her thighs quivering against Nathan's ears as she rubbed her clit onto his tongue, but she didn't squirt; Hosanna, on the other hand, squirted _again_ , her fluids bursting not only onto Nathan's face and back in his mouth, but also against Rebecca's ass and lower back.

Hosanna looked over, and finally noticed Nathan's huge cock sticking out of his shorts.

"Holy shit," she moaned. "Babe, look."

She stepped away from his face and grabbed his cock, jerking him off with both hands.

"That's prettier than any toy I've ever seen," Rebecca said, joining her girlfriend as Nathan pulled off his shorts and leaned back into the sofa, spreading his legs out. All four of their soft smooth hands fit onto his length, and they stroked him up and down together. He pulled off his shirt, getting naked, and put his hands behind his head, enjoying their touch on him.

"Ooh," Rebecca remarked, watching Nathan strip. "Little boy's naked."

"He's dressing for the job he wants," Hosanna teased, rubbing his penis up and down. "Is that right, honey? Are you a horny little manwhore?"

She winked at him, then got out from between his legs to sit next to him and take a hit from the bong, leaving her girlfriend to start sucking his cock on her own. Rebecca wrapped her lips around his head and bobbed, while Hosanna ripped from the bowl they had packed and then offered it to Nathan.

"Uh... actually I don't really know how," Nathan admitted, his fingers wrapped up in Rebecca's hair as she sucked.

"Well here, sweetie, I'll show you how," she assured him, taking another hit, explaining when she pulled the bowl out to release the smoke. Nathan took it and tried as Hosanna handled the lighter. Rebecca looked up and watched them, her tongue spiraling around Nathan's girth, her hands pulling his foreskin down and exposing his pink tip to her lips.

Hosanna pulled the bowl out. "Now _suck_ ," she demanded, and Nathan pulled the smoke into his lungs as Rebecca wondered how similar they might have looked, Nathan handling the bong and Rebecca handling his cock. They were certainly comparable in size!

Nathan erupted into a coughing fit, and Hosanna grinned, placing the bong back on the table and leaning over to join Rebecca at his cock. She gave her girlfriend a little kiss before Rebecca yielded Nathan's head to her: she sucked on the tip as Rebecca went down to lick him up and down his shaft.

"Ooooh my god..." Nathan groaned, stroking both girls' hair as they went back and forth, up and down on him together. His brain was instantly growing more relaxed, a bit cloudier... less "I can't think of it" than "I don't care to try." All he cared about were the two beautiful gay girls slurping each other's spit off of his cock. Rebecca slid her tongue up and joined Hosanna on his head, both of their lips rubbing against his most sensitive spots, his foreskin pulled taught out of their way as they kissed and licked his large pink head directly. Whenever their lips bumped into each other, they would pause for a small kiss, their spit hanging in tiny strings like spiderweb threads, their delicate little fingers caressing his girth down below.

Appearing to communicate silently, Hosanna moved out of Rebecca's way, who wedged herself in between Nathan's legs and pushed him deeper into her mouth. Hosanna put her hand on the back of her girlfriend's head and pushed her even deeper, relieving the pressure to bring her up, and then pushing her down again, bobbing Rebecca's head up and down on his length, fitting almost half of his shaft down her throat. Ribbons of spit showered down onto his crotch, and Rebecca gagged and gurgled enthusiastically against his size.

Then they switched, and Nathan watched in awe as Rebecca pulled away, slobber swinging from the corners of her mouth. Neither girl made any attempt to clean up: Hosanna simply swallowed Rebecca's spit and stuck Nathan's cock into her mouth, saliva and all. Then it was Rebecca's turn to push her down.

Nathan laid back against the sofa, legs splayed, muscles slack, and erupted with cum in Hosanna's throat. Hosanna moaned in surprise and pulled away, just in time for Nathan's load to shoot out across both girls' faces and chests, and over their shoulders, onto the coffee table and the floor behind them.

"Do guys always cum that much?!" Rebecca gasped, her face dripping in semen.

"Hell no they don't!" Hosanna answered, gulping down what had landed in her mouth.

"Damn." Rebecca blinked, wiping some cum out of her eyes, then stood up and went back over to the bong, taking another hit. Hosanna stayed between Nathan's legs, examining his penis from all different angles as if she had never seen one before. Indeed, she hadn't seen a real one since she was a teenager, and she had never seen one as big, even on the internet. She thought guys were supposed to be done after one orgasm, but Nathan seemed to be getting _harder_.

"Hey babe, I'm gonna fuck him," Hosanna said casually, getting onto the couch with Nathan.

"Okay, I'll be right there," Rebecca said from two feet away as she lit the bowl and pulled.

Hosanna laid back against the arm of the sofa, legs splayed across the cushions, and she reached out to Nathan with both hands, fingers wagging in summons. Nathan climbed between her arms, resting their naked bodies together, and she closed her arms around him. His cock pushed against her thigh, and he reached between his legs to grab it and position in between her legs. Hosanna's face was glazed in cum, her smile both sly and relaxed from the pot, but when he pushed inside her, Hosanna's brown eyes burst open wide and her jaw dropped.

"Fuck, that's warm," Nathan grunted as he pushed himself deeper, throbbing inside her with his stiffness.

Rebecca, blowing smoke lightly from between her lips, squeezed herself onto the couch next to Hosanna and Nathan humping on top of her. All three naked bodies rubbed warmly onto one another, Rebecca and Hosanna kissing each other with their cum-soaked faces pressed together as Nathan thrusted into Hosanna, one arm planted next to Hosanna's slim tattooed shoulder and the other wrapped around Rebecca's soft tattooed waist.

As Nathan started to move faster, Rebecca pushed herself back up and perched on the arm of the sofa, spreading her legs and sitting directly onto Hosanna's semen-smeared face, her vagina and its bush pointed directly in Nathan's face. Hosanna pushed her face up into Rebecca's wide ass, running her mouth along her girlfriend's ass crack and licking her anus, as Nathan leaned forward and ate Rebecca's pussy, with his hips still thrusting steadily into Hosanna, his cock always rubbing against her warm, wet walls. Rebecca looked down at them, her bare round tits hanging over Nathan's head, and her fingers gripped the sofa arm she was straddling over as both of her holes were eaten.

Nathan felt Hosanna squirt on him again, her juice gushing onto his crotch as he slid his cock in and out of her, while Rebecca leaned her balance onto one hand and grabbed Nathan's hair with her other. Nathan's tongue was pointed out straight, finding its way through Rebecca's pubic hair to her clit buried within, then flattening to lap it up rapidly. Hosanna's arms wrapped around Nathan's torso as she came, her hands caressing his back down to his ass, and Nathan slid his cock back and forth faster and faster. Hosanna slid her tongue between Rebecca's ass to meet Nathan's at her pussy: the two tongues wrapped around each other in a kiss, rubbing off a bit of Nathan's own cum onto the tip of his nose from where it was dripping on Hosanna's face, before Hosanna returned to Rebecca's butt.

Hosanna swirled her tongue between Rebecca's spread cheeks, onto her asshole, knowing exactly how her girl liked it. Nathan, on the other hand, had only other girls to go off of, and he flicked and rubbed his tongue onto Rebecca's clit as quick and steady as he could, opening his mouth and pulling gently on her labia with his lips, feeling her body writhe and vibrate under his touch. All the while, his stiff cock massaged itself inside the other girl's warm wetness.

He came hard inside Hosanna, shooting his ropes fast and deep up into her, and Rebecca returned onto the couch next to them, ready for her own turn. She was facing the couple lying together, wedged between them and the back of the couch, all three pressing onto each other in a close-packed triangle.

"C'mere, baby," Rebecca muttered to Nathan, and Hosanna put her hands on the boy's hips, pushing up on him, helping him lift himself off of her and turn ninety degrees to his next partner. Hosanna held him snugly from behind, arms snaked under his own, hands clasping his firm thirteen-year-old chest, and he was sandwiched between the two lesbians as Rebecca opened her legs and his ten inches easily reached across her thick thighs and into her hot welcoming pussy. Rebecca pulled him into her, pulling Hosanna in after him, and the two girls locked lips over his shoulder as he grabbed Rebecca's waist and thrusted into her, both girl's faces next to his, smearing his own cum across his cheek before they promptly licked it cleanly back off in between their own kisses.

The couch squeaked with their combined motions, and Nathan slid his hands further back around Rebecca and gripped her fat smooth ass as he pumped himself into her. He heard the two women's tongues slurping across each other, right next to his ear, and he stuck his own tongue out to lick Rebecca's shoulder as he held her cheeks tight and rapidly swung his cock up between her legs inside of her. His cock felt full of pressure, pushing up right from his balls, but he still kept fucking, as his heartbeat spiked and his breathing grew heavy and rapid. The three bodies, radiating heat and coated in a film of sweat, rubbed onto each other more and more urgently, as Nathan felt himself approach the point of no return inside of Rebecca.

"Ooh, are you about to cum, baby?" Hosanna cooed him from behind over his shoulder, still pushing her thin body up against his back. "Cum inside of her, little boy, I want both of us filled!"

Nathan squeezed Rebecca tight and shot his load; they all held onto each other, their gyrations suddenly frozen, as Nathan emptied himself into Rebecca and all three seemed to hold their breaths in a sharp moment of excited sobriety.

Then Nathan gasped and exhaled, and the smoke fell back down onto them.

"Hell yeah," Hosanna said softly, her bangs stuck to her forehead from sweat, slipping off of the couch and grabbing the bong again. Nathan pushed himself up to a sitting position, and Rebecca slowly stood up.

"Babe where's your wallet?" she muttered.

"Wallet... why?" Hosanna asked as she took another hit and handed it to Nathan.

"Babe he's a whore, we gotta pay his cock."

"Oh fuuuuck, you're right!" Hosanna began laughing from her seat on the floor next to the little coffee table, and Nathan hissed as he burned his thumb trying to light the bowl.

He tried again, and pulled a tremendous amount of smoke into his lungs as the two women went off to find some cash for him.

"How much do we owe you?" Rebecca asked, apparently reappearing out of nowhere.

"Uh...oh damn, uh I dunno," Nathan laughed, sitting back up on the sofa, his cock hanging between his thighs. "Let's see... ten for kissing, uh... then what was it?"

"Babe!" Rebecca called over her shoulder. "How much cash do you have?"

Hosanna answered vaguely from the next room, but Nathan waved his hand dismissively. "You guys can just give me what you want, honestly."

All together, the couple had seventy-six dollars and eighty-four cents in cash on hand, and they gave Nathan every penny.

"Do you need us to drop you off somewhere?" Rebecca asked as they got dressed together.

"Hmm... what time is it?"

"Well let's see... it's almost nine."

"PM?!" Nathan looked out the apartment window: it was pitch black. "How the fuck long have we been hanging out?"

"Pretty sure we all passed out together after we got high," Hosanna added, tying her tank top back up.

"Can you guys drop me off at the Cobblestone Plaza?"

"Yeah, that shouldn't be a problem."

Nathan arrived back at Brownleaf National at half-til ten, still fairly stoned and absolutely reeking of pussy, clutching a water bottle for his cottonmouth. He kissed the two lesbians on the lips good night, and sat on one of the long cool benches outside the building entrance, waiting for the pretty teller to get off her shift and make her rendezvous. Like most summer nights in California, it was hardly much cooler than the day, and the scant clouds were lit a balmy purple next to the growing moon. Nathan finished his water bottle and tossed it in a nearby trash can, sitting back down and glancing over at the towering amber windows of the plaza.

Soon enough, the teller emerged with her purse and a lunchbox, her blonde hair hanging loose, her blouse untucked and blazer hanging open for the night. When she saw Nathan sitting there waiting, she paused, like she couldn't quite believe it.

"Hi...!" she exclaimed, almost laughing with surprise. Nathan stood up to meet her.

"Don't act so shocked," he teased her.

"I just..." She swallowed. "I didn't think you'd actually come."

"I never lie to women," he assured her, offering her his hand. "Want to take me to your place?"

"Absolutely," she agreed, taking him by the hand to her car.


	5. Cassandra

**Summary for the Chapter:**

> Nathan's about to get pretty pampered for a homeless teenager when he scores with the absolute dime Cassandra Mulligan: a tall, rich, redheaded 40-year-old businesswoman who not only agrees to pay Nathan for sex, but also brings him up to her luxury hotel suite to milk him for every drop he's got!

On one of the hottest nights of the year, business was booming for Nathan Monroe. The moon was full and bright enough to light the city on its own; but it needed not worry. Nathan was walking the entertainment district, and everywhere he looked were beautiful women in short dresses out to have a good time.

Nathan was also clearly dressed to party. He had tailored his wardrobe over the past few weeks, tweaking it for maximum female attention: tonight he was wearing faded denim shorts, which he himself had cut just below his waist with his thick uncut cock hanging exposed below, and a jean vest several sizes too small, squeezed across his shoulders and covering about as much skin as his backpack would, if he had brought it along with him. These and a pair of shoes were his only garb: he had found both the pants and the vest at a thrift shop and had bought them both for less than ten dollars total.

The return on this small investment turned out to be astronomical. Walking through the thick, humid air of the blistering California night, Nathan was already drenched in sweat despite his near-nakedness, and his wavy hair was plastered down across his face. Across the street were several brightly-lit clubs and a scattering of people going here and there, but he had avoided streets that were too busy or had too many men: the buildings on his side of the road were all closed for the night.

Suddenly a car pulled up to the curb alongside him, and the driver rolled down her window: a skinny, middle-aged brunette in a dark red dress. She, at least, looked more like she was on her way home from work rather than a night out. But that didn't stop her from revving her engine at him.

"Hey baby boy!" she catcalled. "You out for a walk?"

Nathan beamed and instantly approached her window, cock swinging freely as he walked, and he leaned over, ass out, to talk to her through her window.

"Yes ma'am," he responded with a bright grin. Looking into her window, he saw the woman's dress was a low-plunging v-neck exposing her mature chest browned with tans and freckles. "You wanna take me somewhere?"

"Oh I want to take you everywhere," she said. "But first let me have another look at that secret I saw hanging out your shorts."

Nathan stood up straight, his crotch about level with her window, and he pushed his waist forward, dangling his flaccid cock into her car.

"Mmm..." She held his cock in her hand, holding it up before it got hard. "You're hung, boy! How old are you?"

"Thirteen."

The lady gave his cock a few strong jerks, and he flinched and began to grow in her hand.

"You want a blowjob, little boy?"

"Yes ma'am. Twenty bucks."

"All right, hop in."

She let go of his cock, and Nathan quickly went around the car and jumped into the passenger seat as the lady drove off. She didn't go very far until she turned into a dark empty street just a few blocks down, and parked again on the curb, where she turned the car off completely and they both got out and reunited in the back seat.

"Here you go, baby," she said, handing him a twenty and turning on the dome light as he pulled his shorts down around his ankles. She leaned down over his crotch, and he got hard the moment her mouth touched his cock. Wrapping his arm around her waist, leaning back, spreading his legs, and propping her against his torso as she grabbed his shaft and sucked hard on his tip, he relaxed in the back seat of her car and got his dick sucked.

"You like teenage cock?" Nathan asked as she pulled his foreskin back and pulled her lips tight around his head: she seemed unable to fit much of his shaft in.

"Mm-hmm," she moaned, slurping on him and running her tongue around his girth. He reached down her dress's v-neck collar and slid his hand onto her breast. Her tits weren't as firm or smooth as younger boobs he had felt, but her nipples still poked into his palms as he groped her.

"No bra?" he teased her.

Never taking his cock from her mouth, she responded by grabbing his hand and pressing them harder against her breasts, pulling her dress open for easier access.

Nathan pushed her long brunette hair back from her face and grabbed his shaft, his hand now next to hers. He began to jerk himself under her mouth.

"You want my cum?"

"Mm-hmm! Mm-hmm!" She seemed almost panicked with her enthusiasm.

Nathan squeezed his cock, holding her head down, keeping his tip fully inside her mouth as he shot his load. The lady groaned and drank his semen hungrily, still sucking on him like she was trying to empty out a bottle through a straw.

"Whoo!" Nathan pushed his hair out of his face, taking a breath. "Good job, Mommy."

The lady lifted her head off of him. "Thank you, baby boy." She licked her lips and winked at him, and he pulled his shorts back up and headed out into the night, walking down the sidewalk back to his usual spot with his cock still wet and at half-mast hanging out of his shorts.

He stood at the mouth of an alley, trying to keep a low profile and watching passersby for anyone he would want to reveal himself to. It wasn't long before two pretty girls in their late twenties passed by. Unlike the first woman, these two definitely looked like they were out for a bar crawl. They were both pale brunettes: one had chocolatey brown hair, the other jet black, walking together down the sidewalk in thin dresses that hugged their soft frames. They also seemed very sweet: the brown-haired girl had a big smile and a cute, large hooked nose, and the black-haired girl was a bit plumper with smaller features; both wore sleeveless dresses with tops low enough to show off some cleavage, and the plumper girl had on a light flowy cardigan over top of it.

As they approached and passed by the alleyway, Nathan came forward into the streetlight, holding the base of his half-flaccid cock to lift it up and show off its length. The two girls froze and stared, their shocked faces quickly giving way to squeals of laughter as they stopped to look. Nathan spun his cock around like a helicopter for them, taking another step closer onto the mostly empty sidewalk, before stepping back again into the shadows of the alley: a lure.

"Oh my god," giggled the brown-haired girl with the hooked nose, stepping forward to follow Nathan into the alley. Her friend put her hand on the other girl's shoulder, but she was smiling too.

"Where are going, are you following him?!" the plump girl laughed, letting her friend lead the way after Nathan.

"Like what you see?" Nathan teased, spinning his cock around again, although it had gotten a bit stiffer under the two girls' gazes.

"Yesssss..." the brown-haired girl gasped, eyes locked onto Nathan's penis. "I've never seen a dick that big before!"

Nathan pulled his foreskin back: his pink head gleamed in the low light of the alley, and the two girls squealed again. The plump black-haired girl kept her hand on her friend's shoulder, rubbing it, her fingers slipping under the other girl's shoulder strap as she stared.

"Ten bucks and you can play with it," Nathan said, slowly jerking off in front of them. "Twenty and it can go into your mouth." A pause. "For both of you," he added, feeling a bit generous.

"Oh my god," the brown-haired girl said, turning to her friend. "Tell me you have cash."

"I have fifteen bucks!" the other girl cried hastily, digging around in her purse.

"And I've got five! Let's suck his dick."

Nathan backed into the wall in the shadows of the alleyway as the two girls dropped to their knees on the pavement, grabbed his cock, and each went about licking one side of his shaft up and down in short, sloppy laps of their tongues. Nathan's cock shot back up to its full size at the touch of their hands and mouths, and he leaned his head back against the brick wall behind him and groaned, his balls already filling back up.

The two girls moaned loudly together as they both dragged their wet lips along his length, until the brown-haired girl seized his tip in her mouth and the black-haired girl went lower and began sucking on his balls, pulling down on them with her lips as she gurgled in the back of her throat.

"Oh fuck..." Nathan moaned, his mouth stretched open as the two girls pleasured him together, clumsily pulling their spit all around on his member as they rubbed him with their lips and tongues.

The black-haired girl moved up from his balls and straightened, still on her knees, and began running her hands across Nathan's hard stomach as her friend continued to suck wildly. She slid her hands up and grabbed his chest, and began licking his teenage abs. Beneath her, the brown-haired girl grabbed his shaft and squeezed, jacking him off tightly in rhythm with her sucking, until her friend went back down to join her again, licking him wherever the other's mouth left her room.

When Nathan pulled his cock away and began stroking himself, both girls knew immediately to put their faces together and open their mouths wide for his load. It came fast and relentless, spewing thick hot ropes into their faces again and again, each one seeming to shoot faster and further than the last.

"Fuck..." Nathan gasped, his shiny bare chest heaving as he leaned back against the wall.

"How much to fuck you?" the black-haired girl asked, her face covered with cum.

"Yes, please, we'll pay you!" begged the brown-haired girl, semen dripping off her chin and nose, rubbing his abs like her friend just had.

"Please let us fuck you, Daddy!" the brown-haired girl continued, stroking his thighs and cradling his balls. "We'll pay you anything!"

"You don't have to use a condom!" the other girl offered. "You can bust inside of us raw! Just let us fuck you!"

"Thirty more bucks," Nathan demanded, and the two girls instantly coughed up, handing Nathan the cash.

"Can I go first?" said the brown-haired girl. "Pleeeease let me go first!" But she was already turning around and bending over, hiking up her dress, without waiting for an answer. Her friend stood up next to Nathan, wrapping her arms around his shoulders and watching as Nathan pulled the other girl's panties down around her thighs and plunged into her.

"YES!" the black-haired girl cried. "Oh my god, fuck her!"

Nathan pumped his cock into the girl's wet open cunt, grabbing her friend's dress and yanking it down to expose her breasts. She slipped her cardigan off and dropped it onto the ground, pulling her dress open wider for him and smiling as Nathan grabbed her soft white tits, squeezing and rubbing them as he moved his hips back and forth, sliding in and out of the brown-haired girl's pussy.

"Enough, my turn!" the other girl protested, dropping her own panties down around her ankles and lifting up her dress for Nathan to access. Nathan slid out of the brown-haired girl to switch holes.

"Damn you got a fat ass," Nathan muttered, grabbing the other girl's pale wide buttcheeks and hefting them up to stick his cock into her vagina. He grabbed the girl's hips and thrusted into her, his full ten inches gliding back and forth rapidly, and she bent over and touched the ground, backing up into Nathan on all fours as her friend moved over to her and straddled her ass, stacking their holes one on top of the other.

The brown-haired girl's ass wasn't as thick as her friend, but she was firm and toned, and her legs and ass cheeks were spread wide open on top of the other girl. Nathan grabbed her ass cheek with one hand, keeping another on the bottom girl's hip: he began panting loudly, his breath rushing faster and faster.

"Oh my god is he about to cum?" the bottom girl moaned.

"Yeah, I'm gonna cum!" Nathan gasped, pounding deeper than ever, rubbing his cock into the bottom girl's warm hole.

"Fuckin' cum in her, dude!" the top girl cheered, and Nathan released his load into the bottom girl's cunt, groaning as he felt his cum draining into her.

But he kept on pounding, and grabbed the top girl's hips next, pulling her down.

"One more, one more!" he cried, and the bottom girl moved out of the way and watched as Nathan slid his cock back inside her friend, grabbed her thinner waist, and kept on pounding.

"Oh my god I'm still coming," Nathan growled, shooting again, spewing more sperm into the other girl's pussy. He kept thrusting and his cock kept shooting, until his balls were finally empty.

"Oh, fuuuuck..." He finally slowed, pulling his cock out and letting it dangle, softening and drenched, back between his legs.

The two girls straightened back up and slipped their panties off, using them to wipe the cum off their faces before slipping them back on. They looked at each other and giggled, facing back towards Nathan together.

"Thank you, Daddy!" they recited in unison, waving goodbye at him daintily and stepping back out onto the sidewalk, continuing on their way, leaving the cardigan forgotten on the ground.

Nathan stuffed his soft cock into his cutoff shorts, following the girls back onto the sidewalk but heading out the opposite direction to find another trick.

He spotted her quickly enough, after wandering only a few blocks where foot traffic was heavier: a very cute woman walking out of a club, not too much younger than the two he had just met, with dark auburn hair right above shoulder-length, curly and parted naturally down the middle, and a pretty, cherubic face with cute large front teeth and an open upper lip. She may have been leaving a club, but she still looked plenty ready to party, and was wearing a loose, backless spaghetti-strap crop top of thin pink lace that plunged down deep to reveal enough of her chest that the absence of a bra was apparent (the top wasn't much more than bra itself), along with a simple opal necklace, tiny denim booty shorts, and a pair of beige boots.

She was walking in his direction, past several other random people; Nathan stomped up to her boldly, cock straining against his own jean short shorts even when mostly soft.

"Hey there, gorgeous," he said, stepping right in front of her and stopping her in her tracks.

But she seemed completely unfazed: just happy to talk to someone new.

"Hello!" she replied cheerfully, holding up two fingers next to her shoulder, looking his body up and down, eyes pausing on his abs and his bulge. "Why, aren't you dressed to impress tonight!" she remarked.

"I'll say!" Nathan replied. "I love that top, you have a bra on underneath?"

"Uh, no..." She narrowed her eyes at him, but her expression remained warm. "And don't you think that's kind of a personal question?"

"Oh come on. Are you looking for someone to show off to?"

She giggled, and tossed her head to the side looking at him--but her curly dyed hair was short enough to stay still as she moved.

"Well, maybe... but aren't you a bit young?"

Nathan spread his arms, showcasing his scantily clad physique. "Do I look too young to handle a woman?"

"Mm-mmm," the girl shook her head with a big smile.

Nathan stepped right up to her and reached out, grabbing her breasts through her low-cut lace top: people walked by them, many of them drunk clubbers, and none of them bothering to notice how young Nathan was.

"Ooh!" she squealed with delight at his touch. Her breasts were small and supple under his hands. "Aren't you an aggressive young man!" She blushed, both her cute soft face and her exposed chest turning red.

"You got money to burn for a good time?" Nathan offered her.

She draped her arms around his shoulders. "I think I might," she answered, leaning her head closer to him and swaying back and forth.

Nathan's voice was now dropped almost to a whisper. "Ten bucks and you can kiss me right here."

"I think I'll take you up on that, cutie." She tilted her head down and pressed her lips onto his, still swaying side to side. He wrapped his arms around her waist and pulled her closer, and her swaying started rubbing her body against his bulge.

People continued passing by them, and the couple drifted over against the wall of the club, out of the way, holding each other tight, kissing sweetly. Nathan heard someone jeer "get a room!" at them as he pulled on the girl's lower lip and pushed his hips out, pressing his boner onto her body. They leaned against the brick wall of the club together, arms wrapped tightly around each other, and Nathan felt the girl's tongue come out and push against his lips. He opened his mouth and met her tongue with his, and they licked each other, standing still in each other's arms in the dim colorful light of the street, the blur of people and cars washing over them, ignored.

It was a moment that lasted longer than either would have expected, although neither noticed the time. As their tongues explored each other's mouths, and as they held each other close and tight, pressing their bodies together against the brick wall of the club, the money seemed to fade away, and for a few weightless minutes, slurping and licking each other, hugging snugly, with a stream of disinterested people strolling by down the sidewalk, they became a couple that happened to meet on a hot night in California.

The kiss wound down, and Nathan gave the girl a cute peck on her lips. They held their faces close to each other, speaking privately.

"I want to fuck you," she said.

"Yeah?"

"Yeah..." The smile on her face matched her voice.

"Thirty bucks."

"I got thirty." She smiled even brighter.

"Where do you wanna go?"

"Come on, I got a place!"

She grabbed his hands and led him eagerly down the sidewalk, around the corner and down an alley, behind the club she had just left. There was a large parking lot back there, mostly empty except for some employee cars and a few heavily ticketed others. It was surrounded by a high fence, and the only back door was at the top of a small concrete stoop lit by a harsh bulb overhead.

"Looks like you come to this place a lot," Nathan remarked as the girl led him to the stoop.

"Oh yeah, this is my haunt!" she said as she pulled her shorts down and struggled to fit them off over her boots. She wasn't wearing underwear. "I come here all the time."

"Lots of pretty girls in this club?"

"TONS." She finally got her shorts off around one of her boots, and Nathan took a seat on the stoop, pulling his quickly stiffening cock out. The girl stood over him on the steps, her shorts hanging off of one ankle, naked up to her ribs. Her body was slim and soft, and she had a small patch of light brown pubic hair right above her clit. Nathan stroked himself slowly, looking up at her, and she licked her lips looking back down at him, and straddled him, crouching low over his cock.

"Yeah, I bet you could find a ton of customers around here..." She grimaced as she pushed herself down onto his cock and his girth stretched her wide open. She was wide, wet, and hot, but Nathan was thicker, and as his full length entered her, she came almost instantly.

"Oh FUCK!" she cried, sticking her legs out around Nathan's waist, putting her arms around his neck, and bouncing herself frantically on his cock. The bare bulb above the stoop burned down onto them and the parking lot around them loomed dark and bare. The sounds of life on the other side of the building leaked clearly from the streets. It felt like a whole different world back here.

Nathan held the girl's hips and felt her pussy rub and gush up and down his length as she bounced on it. The pressure in his balls was returning, and he watched the girl's small breasts jiggle under her pink lace top right in front of his face, her eyes closed with ecstasy, her cute plump lips hanging open wide and baring her large front teeth. Nathan's lean young muscles flexed out in the open night air as he stayed sitting upright on the top step of the stoop, leaning back, holding himself up by the girl's waist.

The door behind them opened--a slim, tanned college-aged girl with a tight white t-shirt and a short skirt stepped out with a bucket of dishwater, and the clamor of a busy night wafted out behind her.

"Whoa!" she exclaimed, freezing in place as she saw the two lovers going at it on the stoop. But she quickly thawed.

"Yeah, get it, girl!" she cheered, tossing the water over the side of the stoop onto the pavement below.

"Whoo!" Nathan's partner whooped loudly, pumping her fist in the air as she rode his cock, and the two women shared a brief bonding moment before the employee disappeared back through the door.

"Wow, the girls here are really pretty!" Nathan exclaimed, his voice wavering as his partner dropped herself down his cock repeatedly.

"They're so pretty, baby," she gasped, breathless. "You can make so much money here... there's so much good pussy..."

The pressure in Nathan's balls began to spike as the girl's cunt squeezed and massaged his cock.

"Fuck, I'm gonna cum," Nathan moaned, and the girl nodded enthusiastically, riding him even harder, her face and chest a bright flushed red.

Nathan cried out and gripped the girl's hips tightly as he nutted inside her.

The girl's bouncing slowed to a stop, and Nathan's cock rested inside her soaking hot hole.

"Baby..." she moaned, gliding her arms across Nathan's shoulders. "I had wanted you to finish on my tits, but I just got so carried away..."

Nathan perked up. "Five more bucks and I'll cover those tits."

She brightened, and smiled. "Deal!"

The girl got off of his cock, leaving it drenched and glistening with juices, and lifted her top, flashing her cute, perky little breasts. Nathan jerked off to them, and she stuck her tongue out at him teasingly. High on the tails of his last orgasm, this one came quickly like a coda, and more warm white ropes shot out of his cock and splattered across the girl's pointy tits.

"Yay! Wow that's a lot."

Nathan, breathing heavily with sweat rolling down his temples and gathering on his forehead, stood up.

"Were you keeping count of the cash?"

"Uh... no. Were you?"

"Let's see, ten for kissing..."

"Thirty for fucking and five for this! Here!"

She pulled her top back down messily over her cum-glazed tits and, still naked from her waist to her ankle, rummaged about and pulled out her payment.

"There you go, baby! I had a lot of fun."

She gave him a sweet kiss on the cheek, pulled her shorts back up, and returned out to the street.

Nathan, however, was feeling drained and hungry, and with all the money now in his pockets, he decided to do some late-night shopping before returning to his motel room. So he stuffed his cock back into his shorts and headed back down the sidewalk, away from the entertainment district into a quieter part of town.

Here he was getting weird looks more often, as the foot traffic lessened and the lights became dimmer. Still, it wasn't unheard of to see hookers going about their business after hours like that... they were just usually women.

He headed into a 24-hour grocery store a couple of miles away from his motel (the only one he knew to be open at this time of night), feeling a bit self-conscious of his appearance now that he wasn't actively looking for tricks... not to mention deathly cold as the strong A/C hit him like a spear as he stepped through the automatic sliding doors.

Cradling his mostly bare body against the frigid air, Nathan grabbed a basket and began scavenging for groceries, making note of any employees he saw standing around even though he was fully planning on paying for his items. He headed to the bread aisle and stood in front of their selection. The dark whole grain bread he liked was nearly five dollars per loaf. Maybe he could buy some things and steal the rest? Oh but he was standing there virtually naked, how could he possibly sneak any food out?

There was suddenly a severe clattering of heels on the hard linoleum floor, and before he could turn his head to look, a long, pale hand shot out in front of his face and grabbed the most expensive variety of bread in the entire aisle.

He looked up at the hand's owner, and suddenly felt like a virgin again.

She was towering over him at a full six feet tall, with deep, dark red hair flowing like wine across shoulders draped in a crisp black blazer. Her face was sharp and her cheeks bright and rosy; her eyes were narrow, glowing bright but dark in color, and her lips were thick and red. She was regarding him with a muted curiosity, dressed in a pitch-black business suit: a half-buttoned black blouse hinting at the black lace bra underneath and high-waisted formal black pants standing stiff around her long legs right down to her black heels.

She smiled at him slyly.

"Out late are we, young man?"

Nathan gulped.

"I'm just... uh, l-looking for some dinner...."

A stammer! He had stammered at a beautiful woman! He hadn't done that in years! He blushed deeply and tried for a grin.

The tall, redheaded lady dropped her bread into her shopping cart and regarded him with arms crossed. She sniffed the air. Nathan turned pale: he instantly understood that she had recognized the smell of sex.

"What's your name?" she asked him curtly.

"Uh, Nathan."

"What are you doing out so late, Nathan?"

"Just... getting some dinner, like I said--"

"How old are you?"

"Thirteen."

"Are you here by yourself?"

Nathan swallowed, and composed himself.

"Listen, ma'am, I'm just trying to buy food, you don't have to ask about every--"

"Are you here by yourself?"

Nathan stared at her, silenced, until he could answer.

"Yes ma'am."

"Hmm. I thought so. Out dressed like that."

She pulled her blazer off and draped it around Nathan's shoulders.

"Now pull it closed around you, child. Not very subtle tonight, are we?"

Nathan blinked, slipping his arms into the blazer and buttoning it up. It was long enough on him to cover his particularly short jeans.

"Put that basket away now, boy. I'll buy your groceries tonight."

Nathan beamed. "Really? Oh, thank you! That's incredible!"

The lady gave him a rather restricted smile. "Now let's get to shopping, shall we?"

She walked off, and Nathan, after standing awestruck for a moment, hurried on after her.

She looked like her shopping was almost done, with her cart mostly full.

"So what do you want, Nathan?" she asked him.

"Uh, well actually I was looking for some bread back there--"

"Yes, I know, this is yours," she said, gesturing to the expensive loaf she had picked out.

"Oh, wow. Uh, thanks. So what's your name?"

"My name is Cassandra, sweetie. And you, Nathan, need to be more careful about going out and about like this."

"Uh, what do you mean?"

"Oh come now, boy. I'm not an idiot. I know a street walker when I see one. That getup and that smell would set off anyone's alarms. And you're lucky I spotted you before some damn cop did." She winked down at him.

Nathan frowned, and shrugged. "Well... I was working. I live off Lexington, I didn't want to walk all that way just to change clothes!"

"Sounds like a hard life."

"I mean, I guess. I make money, and I get laid. Pretty scary but also pretty fun."

Cassandra nodded, continuing to walk on, and even though it was supposed to be Nathan doing the shopping, she seemed to be picking out items for him without his input. He looked up at her profile as she walked beside him: her nose was small and straight, its tip curved slightly upwards, her lips ever so vaguely pursed, her eyelashes long and thick around her shadowed eyes which were emphasized startlingly by her dark red hair.

She took a bag of dry pasta off the shelf and dropped it into her cart, never looking at him.

"I can feel you staring, young man," she said with a mixture of sternness and amusement.

"Oh! Uh, sorry, I--"

"Are you still taking clients tonight?" she asked, finally turning her head and shoulders to look at him.

"Clients? Uh, well always."

"I mean you're not drained yet, are you? A boy of your age probably has a lot in him compared to an older man, but I don't know how busy you've been tonight."

"Oh yeah, I have more in me! I just need some food, you know."

"How many women have you been with tonight, Nathan?"

"How many? I had sex with three and got head from another."

"That explains the smell. Is that a normal haul for you?"

"Pretty standard, yeah. I usually look for women until I have enough money for food and my room."

"You said Lexington?"

"Yes ma'am."

"God, what a fucking pigsty. No, that won't do. I'm taking you to my suite."

"Your suite?!"

"I'm on the eleventh floor of the Romani on 2nd and Seaward. Would you like to come there with me?"

"Oh, absolutely! Damn, the Romani? That place is a palace!"

"It sure is."

Cassandra reached out and ran her fingers through Nathan's hair.

"But no funny business until we're alone, understand? You're my nephew, if anyone asks. Keep that blazer closed tight, it at least doesn't make you look naked."

Nathan nodded, pulling the collar of the blazer close across his chest.

Cassandra paid for a bevvy of groceries for Nathan, none of which he asked for or was planning on buying, and he followed her out to her car in the store's parking lot.

"What are your rates?" she asked once they were in the car.

"Ten for kissing and touching, twenty for oral and thirty for sex."

"So you never make more than sixty dollars for a full service?" she interrogated, pulling out onto the road towards the coast.

"Well, that's the cost of my room per night. So as long as I get at least two women who want to do everything--"

"That's a very narrow margin, Nathan."

Nathan sighed.

"Yeah... but I'm young. And illegal. I have to be cheap enough to be impulsive."

Cassandra nodded in understanding. "Well put. How long have you been doing this?"

"All summer."

"Are you going to go to school?"

"What? Hell no. I'm not going back to my parents and all that life. I took this risk for a reason."

She nodded again.

"Well, Nathan, I can't help you there. I have a lot on the line here in Bay City and can't be caught with a child. Tonight only, understand?"

Nathan nodded. "Yeah, you do you, ma'am."

"Good. But for this one night I want to help you out. Okay? You can rest easy."

"Thanks."

"Oh, don't sound so cynical. You're about to get paid for a full service, a free luxury hotel suite, room service, groceries..."

She glanced at him as she drove.

"I can't imagine that you don't drink."

"Sometimes."

"Well I'll mix you up something good. I like you, Nathan. You're very sexy and sweet, and I already saw how much you're packing in those skintight shorts. I think you deserve to be lucky."

Nathan smiled, pulling Cassandra's blazer around him closer.

"You remind me of my old teacher."

"Do I, now? Were you lucky with her, too?"

"Oh yeah. Very."

Cassandra smiled at him, ruffling his wavy black hair again.

"You're very cute. And I know you're attracted to me too, from the way you keep staring. So I'll let you have me. And I've always had the privilege of being very selective of the men I sleep with."

The Romani Hotel on Seaward Avenue was a towering beacon of light that could easily be seen from the ocean, like a lighthouse. Radiating gold in the night, it was cordoned off by elaborately-kept grounds and accessible by a long wooden walkway.

"This place is incredible!" Nathan gawked, staring up at the glowing tower before him as they headed towards it. "What are you doing here?!"

"Business," Cassandra answered simply. "If they're going to make me travel hundreds of miles away from my home, then they damn well better set me up in the best spot in town."

"Man you were right. Lexington Avenue really is a fucking pigsty."

"Don't have to worry about that tonight," she reminded him silkily, rubbing his back. "And remember, keep a low profile and say you're my nephew if anyone asks. Hold that jacket closed."

Nathan pulled Cassandra's blazer tightly around him, hiding the fact that he was largely nude underneath, as they entered the echoing brass lobby of the hotel together. This late at night, the place was mostly empty except for the bored-looking concierge who only perked up to ogle at Cassandra as she checked back in and ushered Nathan on with her, down the amber-lit hallway with its lush carpeting and clean walls, into the elevator.

"How much does this place even cost?" Nathan asked. Even the elevator was wide, shiny, and brass.

"I don't know, it's not my damn money," Cassandra said boldly as the elevator dinged and she led him into the eleventh-story hallway.

It wasn't like most hotels Nathan had seen. There weren't rows of doors all lined up next to each other. Instead, Cassandra's room seemed to have almost an entire side of the building to itself. And indeed, as she unlocked the door and led him in, she pretty much did. Her suite was enormous, expanding in all directions with a wet bar and stocked refrigerator, cushy lounge with a conversation pit, fireplace, wide windowed walls leading out to a balcony with a view of the ocean, and a door to the far left leading to the bedroom.

"Holy shit!" Nathan cried. Cassandra smiled to herself as she locked the door behind her, dropping her purse on the nearest soft red chair and turning to face him, still carrying their groceries.

"Give me my blazer back, young man," she said sternly, and Nathan nodded hastily and pulled the jacket off. She took it and dropped it on the chair with her purse, regarding Nathan before her, now half-naked again like he had been when they met.

Her eyes traced him slowly, drinking in his cute swooshing dark hair hanging almost into his brilliant blue eyes, his handsome, sharp jaw, his lean chest, hard abs, sculpted arms, giant bulge, and trim, firm legs. Her gaze hesitated on his crotch, and his penis seemed to sense her eyes on it, tingling with excitement when it was looked at.

But then she turned around and walked away, heels clacking loudly across the suite's linoleum flooring, and stashing their food into the kitchenette and then heading to the suite's private wet bar.

"Well, Nathan," she said as she approached bar. "Go ahead and take off your shoes, make yourself comfortable." Then she looked over at him, her dark shiny eyes hardened. "Do not undress yet."

"Yes ma'am," Nathan said, kicking his shoes off and setting them next to Cassandra's heels.

"Are you cold, Nathan?"

"Not really."

"Good. Have a seat at the bar, I'll make you a drink."

Nathan did so, watching as Cassandra mixed him a cocktail with an experienced grace. She looked absolutely stunning with her sharp black blouse bringing out her beautiful tumbling burnt-orange hair, which in turn accentuated her hearty red face and her sweet pink lips.

But as she went about making Nathan's drink, there was a kind of heavy silence in the air that he didn't expect. After a few moments, he realized Cassandra was leaving him open to begin the conversation.

"How often do you travel in this kind of style, Cassandra?"

Cassandra smiled and served him a bright green citrus drink with a kiwi slice floating on top. She seemed pleased that Nathan had taken her opening: he had passed a test.

"A few times a year," she said, beginning work on her own drink. "More often nowadays. And the more I travel, the more I get compensated.

"What do you do?"

"I'm Chairwoman of the Board for CTEF. That's a national investment firm. This week I'm meeting with several of our new partners in a summit here in Bay City." She looked up at him, gauging the teenager's reaction to her answer.

"So you're just fucking rich," Nathan clarified.

Cassandra smiled. "Yes. Good job."

Nathan took a sip of his drink. Cassandra had hid the alcohol well with the sweet fruity concoction, but Nathan, who was by no means an experienced drinker at thirteen, still flinched getting it down.

"Hurm." Nathan cleared his throat. "Uh, what were you doing when you were my age, then?"

"You're thirteen? Well I'm forty now--"

"Forty? Jesus Christ you look good."

"Why thank you! But when I was your age I was far from having adventures like you. I was... let's see, I was still in middle school, being forced to play golf by my curmudgeonly old grandfather."

"I bet you could have fucked for money if you tried."

"Oh believe me, I knew what men thought of me even back then."

"It seems most girls did."

Cassandra nodded, taking a drink and leaning over the bar towards Nathan.

"That's because the men who leer at us aren't like you."

Nathan looked away, suddenly shy. This seemed like the only context in which shyness actually appealed to Cassandra, who drained her drink and came around the bar to sit next to Nathan. She reached out and rubbed his arm as he took another sip.

"Would you like to take a bath with me?" she asked.

Nathan gulped his hard drink down and nodded. "Absolutely. I have a lot of, uh, other women on me right now."

"Ah, yes. Well we won't be washing them away quite yet. Come join me in the pit."

Cassandra left her empty glass on the counter and went over to the lounge of cushy red chairs in the middle of the suite, next to the wide glass walls. Nathan followed her, gulping down some more of his own drink.

"I think it's time you showed me what I'm paying for," Cassandra said, taking a seat on one of the armchairs and crossing her legs lithely at the thighs.

"Yes ma'am," Nathan said, setting his glass down as well, and dropping his shorts, letting his massive half-erect cock--and the smell of all the vaginas it had been inside that night--flip out into the open air.

Every muscle in Cassandra's body tensed at the sight. Her jaw clenched itself, and she covered her mouth with her hand as she stared. Nathan's cock grew stiff rapidly as she gazed at it, and was soon standing tall in his lap, curved slightly skyward, his wide head stretching his foreskin around it. Cassandra lowered her hand and stared with a curious expression: she seemed adoring, enamored even, with her mouth open in a silent "ooooh" and her eyebrows curved upwards in the middle

"Baby..." she moaned, absently undoing a button on her already half-open black blouse, giving more of a glimpse of the black lace bra underneath. Nathan's cock throbbed visibly as he sat before her, but he clenched his fist in discipline and sat still, letting her watch without touching himself (or her, for that matter). He took another swig of his drink, the ice falling against his upper lip as he finished it. His thighs were trembling slightly. This woman really did make him feel his age.

"Let me get you another drink," Cassandra said, standing up and walking back to the bar. "You keep that cock hard for me, okay young man?"

Nathan looked forward at his stiff erection hovering in front of him. It didn't feel like it was going anywhere anytime soon. He heard the clinking of glass and ice as Cassandra mixed him a new cocktail.

"Enjoy," he heard suddenly as Cassandra returned behind his seat, handing the drink off to him and then coming around his chair and dropping to her knees between his legs.

"Drink up," she told him, rather sternly, as she grabbed his cock in both her hands. "I'm working you until morning."

She bowed her head and opened her mouth, and Nathan threw back this second, stronger drink as Cassandra's slick lips slid around the head of his cock.

She pushed her head down deeper, deeper on his shaft. Although she gagged a bit, and drool leaked out of her mouth down to his crotch, she fit more of him in her mouth than almost any other woman had recently. Nathan watched her go, mouth hanging open, holding his half-finished drink in one hand. Cassandra pulled herself up and down on him, stroking him tightly as she sucked, looking up at him with her dark, thin eyes. She regarded his expression, winked at him, then increased the speed of her sucking and the tightness of her lips and hands on his girth.

"Oh, fuck..." Nathan took another swig of his drink, then dropped his head back against the comfy armchair and closed his eyes, feeling his cock squeezed and rubbed and soaked by Cassandra's mature mouth. Nathan stroked her dark red hair as she sucked, finishing his drink and dropping the glass carelessly on the floor next to the chair.

She slid his cock out of her mouth with a slurp. "You really have had a lot of women tonight," she remarked slyly. "I can taste them." She licked his tip, sliding her tongue around on his head with his foreskin pulled back.

"But now I want some cum," she continued, slowly stroking his length with both hands. "And you're on the clock, so you'd better deliver, young man."

She dove back in, sucking and jerking him faster and harder than ever. The rest of Nathan's body went limp; his legs slid out on either side of her, his shoulders sagging and his arms lying still by his sides.

"Oh my god..." Nathan moaned as the pressure began pushing up his shaft. "Fuck..."

"Mm-hmm." Cassandra held eye contact with him as she moved up and down on his cock, her hands jerking his length hard, her lips slurping and pulling on him with her tongue licking him strongly.

Nathan groaned and came, his lax body tensing up and his young muscles flexing as he unloaded into Cassandra's mouth. She moaned with satisfaction, her lips tightening around his girth as she sucked his cum down and swallowed it all. Then she released him, letting his cock stand up tall, shiny and dripping with her saliva.

She stood up, licking her lips clean and leaving Nathan sitting in a heap in the armchair.

"Now let's get serious," she said, heading back to the bar. Her heels charted her path behind Nathan as he took a deep breath and regained his bearings. His cock had dropped somewhat, but was still thick and heavy, sagging to one side as it wasn't standing up straight anymore.

He rubbed his eyes and was about to turn around to see what Cassandra was doing, when suddenly the entire suite filled with smooth, rumbling R&B, with speakers, it seemed, synchronized in every room.

Cassandra returned in front of him with two fresh glasses; he could smell the vodka from where he sat.

"You've passed your audition, sweetie," she told him, handing him one of the drinks. "Now let's get cleaned up so we can have some real fun. Follow me."

She turned on her heel and clacked her way to the bathroom, and Nathan quickly got up and followed her, leaving his shorts behind on the floor and taking a swig of his strongest drink yet, his half-flaccid cock dangling between his thighs. In front of him, Cassandra's wide hips swung in her black fitted pants. She looked back at him and winked as she approached the bathroom door, letting them both in.

It had to have been the nicest bathroom Nathan had ever seen. All spit-shined tiles and gleaming white porcelain which looked like it had never been used, with a giant walk-in shower encased in glass walls, and--the pièce de résistance--a deep, wide jacuzzi bathtub, with bronze knobs that looked like gold, and a smooth rounded bench along the entire perimeter for easy sitting. The smooth, deep music Cassandra had put on flowed from a speaker set in the corner of the sink. Saxophones and bass droned soothingly as she took a sip from her drink and locked the bathroom door behind them, finally taking off her heels and setting them next to the door.

"You've had a busy night," she remarked, going over to the bathtub. Her voice had softened considerably since the blowjob. "How about you take that cute little vest off and we'll wait for the water to get hot together?"

He did as he was told, removing his last garment as Cassandra got the water started and took another sip of her drink, walking up to him and grinning.

"I've seen you looking at my chest since we met," she told him. "Put that glass down and you can take out my breasts."

Nathan clanked his drink down eagerly on the sink, reaching out and unbuttoning Cassandra's black blouse. It fell open: her black lace bra swelled with her full, mature breasts, her skin pale and smooth below it on her firm flat stomach, and flushed red above on her chest. She simply stood there and watched him with a smile as he pushed her shirt open wide and unclasped her bra from the front; it slipped off her breasts, hanging on just by her shoulders, her bright white tits and wide pink nipples fully on display for Nathan, above her firm, flat belly.

"You look like you've undone your fair share of bras, hmm?" she teased him, taking another drink and slipping off her blouse.

"Yes, ma'am," he answered, reaching out and grabbing one of her tits. "All in a day's work."

"Oh, I'm sure." She dropped her bra on the floor, standing topless in front of him, letting him fondle her tits as he pleased. She smiled, watching him enjoy himself, pushing a lock of dark red hair behind her ear and closing her eyes in her own pleasure from his hands on her.

"You know how to touch a woman, my boy," she said, stepping away from him and tending to the bathtub. She checked the temperature, closed the drain, and added her soap and oatmeal solutions. Then she unbuckled her pants and pulled them off and down, folding them and setting them on the floor next to the sink. Finally, she removed her panties, placing them neatly onto her pants, leaving her naked. She never so much as glanced at Nathan the entire time, who watched her as he retrieved his glass from the sink and drank. Her ass cheeks were round, flushed red like her chest and face, and wobbled when she walked, but her legs were firm and toned, just like her tight stomach and her lean arms.

"Join me, Nathan," she said calmly, stepping into the bubbling bathtub as it filled. Nathan dipped his foot in the water: it was perfectly hot, cleansing without burning. He stepped in, holding his glass carefully; the drink was very strong and he was struggling to finish it.

Cassandra sat on the porcelain bench submerged under the water, taking another sip of her drink before placing the glass on the deck of the tub next to her. She watched patiently as Nathan waded across the tub and sat down next to her. Seeing where she had put her glass, he did the same, placing it on the deck out of the way.

"Good boy," she said with a smile. "Now kiss me."

Hands free, Nathan leaned over into her and grabbed her waist under the water, pushing his lips onto hers and pressing his hard cock onto her thigh. She pulled on his lower lip between her own, holding his shoulders and scooting closer to him, and then opened her mouth and let out her tongue. He felt her licking his mouth and licked her back, their tongues rubbing together and their mouths open wide against each other. He stood up in the tub, hunched over her, and straddled her lap, his dick rubbing onto her firm, toned stomach. She wrapped her arms around him and pulled him close, until his balls rested on her thigh, and moaned deep in her throat as his tongue explored inside her mouth.

They kissed deep and long, probing into each other's mouths, their tongues and lips smacking loudly. Cassandra held Nathan tightly against her toned, mature body, pressing her breasts against his young chest and letting him hump her waist with his cock as he straddled her. Saxophone and bass washed over them from the bathroom speakers. Nathan moaned in pleasure from the feeling of Cassandra's tongue and skin and of the hot soapy water soaking them both. Cassandra brought her hands up to stroke Nathan's wavy hair, and water splashed and poured between her fingers and across his crown, suds distributing through his dark locks.

"Dirty boy needs a bath," she said softly, rubbing soap across his lean shoulders and chest, then lifting her hands to his head and massaging his scalp. "You need me to wash your hair for you, sweetie?"

She made to stand up, and Nathan got off of her as she went and grabbed one of the shampoo bottles perched on the edge of the tub's deck.

"I want my boy squeaky clean for when he finally gets to have his way with me," she said. "Get wet."

Nathan ducked under the water, his face and hair now seeped in heat. He lingered for a moment: under water, it was as if nothing was happening, and it was peaceful.

Not for long though. When he stood back up and broke the surface, he was presented again with Cassandra's gorgeous 40-year-old nakedness, fit and hearty pink to match her dark red hair. She was taking a sip from her drink before replacing the glass and coming over to him with a hand full of shampoo. A moment's peace paled in comparison to a night of action.

"Turn around young man."

She pressed her tits against his back, grinding her crotch sensuously onto his firm thirteen-year-old ass, as she began to lather and massage his hair with a billowing plume of shampoo, bunching his hair in her hands and washing it deeply. He closed his eyes and groaned, liking this new feeling of her fingers on his scalp and his hair soaked in fresh clean heat.

When she was done, he ducked down again, underwater, rinsing his hair clean. By the time he came back up, Cassandra was already drenched herself, holding he shampoo bottle again.

"Your turn, baby boy."

"You know, I don't think I've ever washed someone else's hair before," Nathan remarked playfully, squirting a ball of shampoo into the palm of his hand.

"Well, a boy in your line of work will have plenty of opportunity to practice when he becomes a father," Cassandra teased with a wink, stepping over to him and taking a seat on the tub bench.

"Oh, I've been a father for a while now," Nathan responded, reaching forward and lathering Cassandra's rich dark hair with both hands, face-to-face. Her eyes closed, but her face tilted up as if she was still looking at him. Below, the head of his cock peered out from the surface of the bath.

"I'd be more surprised if you weren't," Cassandra said, grabbing his cock under the water as Nathan bundled her long hair up in his soapy hands. "Mmm... a big young cock, and a nice hot bath after a long day," she moaned, almost to herself. "This is a good night." The hand not holding his cock reached out further and fondled his balls. The combination of Cassandra's long, mature hands as well as the hot water on his genitals made them start tingling again.

Nathan gathered some water in his hands, pushing them through her hair, sliding many of the excess suds out into the tub. She opened her eyes and they gazed at each other, almost within kissing range again. But instead of kissing her, Nathan tightened his grip on her hair, suddenly seized with an urge to be pleasured again. He pushed down on her head, and she resisted with surprise, her eyes widening and her jaw hanging lower. Her mascara was getting smeared in the bath, and it made her look truly irresistible. The tip of Nathan's cock quivered right above the water, and he pushed her down again, his sudsy hands clamped onto her crown. Cassandra offered some resistance again, but moaned wordlessly as Nathan kept pushing her down towards the head of his cock, and her hands went to his hips as she gave his tip one single kiss and then attempted to stand up.

But Nathan kept her down with his lean, strong young arms, and lifted up one leg onto the bench next to her, pulling his cock fully out of the water. His ten-inch cock stood across her chest as she sat next to him, water dripping down her face. Cassandra looked up at him, straining against his downwards push, and her eyes were aflame. She slowly opened her mouth: a challenge.

Nathan set his jaw and pushed Cassandra's head down to his cock, her widely parted red lips inching closer and closer to his hovering tip. Cassandra opened wider, but pushed harder against him, water splashing and spraying off of her hair and rolling between his fingers.

His head passed between her lips, and they closed around it. Cassandra sucked off the hot water from his cock and replaced it with the softer warmth of her mouth, but just as quickly yanked her head back away from him. She pushed herself back up, and Nathan grimaced and pushed her back down again. Cassandra's mouth opened for him, and he passed between her lips again.

She sucked on him again, harder this time, and he pushed his cock back and forth into her mouth; but Cassandra still fought against him, and only two or three inches were allowed in her mouth before she pulled back again, moving out of his grip, and ducked under water to rinse her hair out.

Nathan stood there, lowering his leg back into the tub, feeling his sweat mix with the water from the bath. Cassandra emerged again, her face washed of makeup. Her eyes looked smaller and the skin around them was pale. She winked at him and approached him again.

"Tits next," she said, taking a bottle of body wash and pouring some onto her chest. "You want to wash them, sweetie?"

Nathan nodded and obediently waded over to her and grabbed her tits, massaging the soapy lather across her chest, around and under her breasts, squeezing and rubbing her as the soap oozed between his fingers, running down his arms and her stomach. Cassandra closed her eyes and enjoyed the feeling of his hands on her, leaning her head back and moaning as he kneaded her tits, swirling soap around on them, pushing them up and down and side to side as he played and lifted them about.

She turned around, backing into him until his cock pressed onto her ass under water.

"Here you go, baby," she said, reaching back, taking Nathan's wrists and bringing his hands under her arms to cup her breasts from behind. Nathan moved in closer, pushing his cock firmly into her cheeks, and rubbing her tits in wide, circular motions. He bent his knees, positioning his cock between her legs, but she reached down and gently slapped his manhood away, stepping forward away from him.

"Not yet," she said sternly, climbing onto the tub bench on all fours, soaked ass sticking up in the air. "You're not done washing me."

Even through the hot water and scented soaps, Nathan could smell Cassandra's arousal coming from between her legs.

"You..." He hesitated for a moment. "You want me to wash your pussy?"

"And my ass!" she answered as if it were strikingly obvious. "Come on boy, get to it!"

Nathan lifted a handful of soapy water and splashed it down onto Cassandra's ass. She lowered herself so Nathan could rub suds onto her just like he had for her tits: he ran his dripping hands around on her wet ass cheeks, holding and squeezing them. He pulled her cheeks apart and saw her small dark asshole, and washed it with his bare hand, running his fingers up and down her ass crack. Her slick pussy radiated hot underneath, and he lifted up another handful of water and lathered her lips, running his fingers along her pink folds. Cassandra moaned and bit her lip, sticking her ass out further for him.

He had never examined an asshole up close like this before, or spent this much time touching one. He had always focused primarily on vaginas. When he started to massage the soap and hot water onto her anus, Cassandra moaned again just like she had when he had lathered her pussy lips. So he washed both at once, one hand rubbing her asshole and running wet and sudsy up and down along her crack, and the other masturbating her.

Cassandra's hand shot out and grasped the edge of the tub; her head was bowed, facing away from him ass-first, so he couldn't see her face, but her body language was plenty: her smooth, pale back rippled, her butt trembled and her fingers curled against anything they could grab. So he kept going, watching her response closely: he lathered more soapy water into her ass crack and ran his hand between her cheeks back and forth: her whole body shivered despite the heat. His fingers rotating around on her cunt suddenly plunged into her hole, and she squealed with hypersensitive surprise. Her back arched, and he felt around inside of her with two fingers, feeling her hot wet walls and sensing the bright bolts that ran through her when he touched her somewhere good.

"Nathan...!" she gasped, pulling away. She was almost out of breath, sitting on the bench, leaning back against the edge of the tub's deck.

"Nathan..." she moaned again. "I think that's enough. Let's get dried off and go to the bedroom, okay?"

"Yes ma'am," Nathan said, getting out of the tub, and for once it was he who led the way even though it was Cassandra's idea, finding the towel closet himself and handing her one. They dried off together in silence. Cassandra's whole white body was flushed bright red, and Nathan watched her tits and ass jiggle as she raised her towel to dry her hair. He was still stiff as a board, his cock pointing at the ceiling.

"You're very good, little boy," Cassandra said, regaining her composure. She dropped her towel to the floor and held out her hand. "Time to get into bed." She nodded at the next door, beside the one that led into the suite's lounge.

Nathan took her hand and led the way himself, opening the bedroom door and guiding Cassandra inside. His hard cock wagged back and forth, and Cassandra noticed with an even brighter blush.

Cassandra closed the door behind them, and Nathan turned to regard his room for the night.

It didn't look like any hotel room he had ever seen! Instead, it looked like someone's real, private bedroom in their mansion, with the wide king-sized bed, the unique floor rugs in front of every door and desk, the dark wood panel walls, and of course the wall-sized sliding glass door which doubled as a giant window and led to a balcony overlooking the sea.

"Well shit," Nathan said, almost to himself. "I can see why you hate Lexington Avenue so much now."

"Mm-hmm," Cassandra moaned, grabbing his hand and leading him to the bed. She sat on the edge and pulled him up next to her, and they kissed again, licking each other's tongues enthusiastically. Nathan wrapped his arms around Cassandra's hips, and Cassandra grabbed his cock as it pushed against her waist, jerking him off with both hands gripping his length like the hilt of a sword. They swirled their tongues around on each other, Nathan letting go of her hips with one hand to grab her breasts, squeezing and hefting them with splayed-out fingers. The heat of their long bath had flattened her nipples, but Nathan still rubbed them under his fingertips, and they still sent shivers of pleasure through Cassandra's body. Precum leaked from his hard cock onto her hands as she stroked it, repeatedly squeezing and releasing his foreskin as her grip slid up and down his shaft.

When the kiss ended, Cassandra let go of Nathan's dick and moved away, crawling across the bed on all fours, her legs open and her ass up in the air like she had it back in the tub.

"Eat me," she demanded simply, resting her head down against the pillows, keeping her ass sticking up. Her pale toned legs held her ass up almost at Nathan's eye level as he crawled obediently after her, her firm cheeks spread wide, both holes exposed. He slapped both of his hands on her cheeks, and she giggled, closing her eyes and relaxing in anticipation of his tongue.

The smell of pussy hit him strong like a wall, and the visible tightness of her holes seized him with desire even apart from her instructions. He stuck his face into her ass, sticking his tongue out and licking her labia in fast, long laps of his tongue. Cassandra squeaked in delight at Nathan's rapidly roving tongue, as he slid it up and down her pussy lips, swirled it onto her clit, and burrowed it into her hole. As he licked her, pushing his face between her legs for maximum reach of his tongue, his nose pressed against her ass crack, and she moaned as his hot breath tickled her asshole.

Cassandra's juices soaked her labia, and Nathan slurped them all up as fast as she produced them, licking her clean over and over, his tongue enveloped in her lips, its long rough texture massaging her pussy and electrifying her clit with every instance of contact. She gushed onto his tongue, her muscles tensing under his hands, and still Nathan kept licking, and pulling on her folds gently between his teeth, finding purchase on her lips and the bump of her clit and sucking tightly, which caused her to squeal and gush yet again, until the process repeated itself.

Then he moved up to her asshole, gripping her cheeks and holding them apart as he began to lick her freshly washed anus, swirling his tongue around the dark hole and then pushing against it, trying his best to enter. Her asshole was too tight for his tongue to open, but she seemed delighted by his efforts, her legs shivering and her breath bursting in labored gasps after extended periods of being held.

He dragged his tongue up and down the length of her crack, tasting her skin, feeling her burst with pleasure every time his tongue rubbed across her asshole. His fingers left red impressions on her pale ass cheeks as he gripped them fully with spread-out hands, and as he licked her, he could feel her cunt, still soaked, grazing his chin.

"God, put something _in_ me!" she cried, slipping herself out from under his hands and mouth. "Get on your back, little boy. I'm going to ride a load out of you."

She put her hand on his chest and pushed him back without waiting for him to move: he fell back onto the pillows, his hard cock resting across his stomach, reaching to his chest. She grabbed it, straddled, and lowered herself down on it.

Cassandra's dark, narrow eyes burst open with sensation, suddenly girlish, and she pushed herself further and further down his length. Nathan laid there, passive and quite helpless, mouth agape as his cock was squeezed by the hot tightness of her mature 40-year-old vagina.

Cassandra squatted over him, about eight of his ten inches stuffed inside her, and she tied her dark red hair back into a tight, severe bun, managing it out of her face before she leaned over him, her breasts pushing onto his collarbone, her face right above his, arms wrapped around his shoulders, and she began to ride his cock, steady, long pumps of her hips that dragged her entire body back and forth across his. Nathan grabbed her ass and squeezed her cheeks, his cock pulled and pushed on by her wet cunt, and he looked up at her gorgeous adult face. She was flushed red, her dark eyes sparkling, grinning wickedly down at him.

"You like older women, baby boy?" she teased him, going back and forth on top of him, massaging his cock with her warm inner walls.

"Yes ma'am!" Nathan exclaimed, hugging her torso tight as she fucked him.

"I bet they like you too, huh? This big fucking cock. You're a cute little boy, huh?"

"Mmmm..."

"Say it. Tell me you're a lady's man."

"Uh... uh... I'm a lady's man!" Nathan could barely speak with his cock being stroked so deftly and tightly by her vagina. Virtually all of his length was fitting inside of her.

She held his face lovingly, almost maternally, as she rode him, staring him right in the eyes. He looked back, sapphires on full display.

"Do you like fucking raw?" she asked.

"Mmm... y-yeah..."

"Do you like cumming inside of strangers?"

"Uh-huh...!"

"Do you care what happens next?"

"No! Oh fuck... mmm..."

"Maybe I'll let this big cock cum inside of me. How's that sound?"

"Oh god... fuck!"

"Yes... baby..." She stroked his cheeks and jaw sensuously with her long white hands, smiling at him, her body roving about on top of his, their faces almost touching. Nathan began to feel that wonderful pressure in his balls, building to a release right up into her.

"Cassandra...?" he whined. "It's gonna happen soon..."

"Let it happen, baby," she cooed him softly, her ass bouncing up and down on his cock. "Let it all out."

Nathan's beleaguered panting suddenly froze, and a tiny squeak escaped his throat as his body tensed, and released, his orgasm exploding deep into Cassandra's pussy. Cassandra closed her eyes in bliss, smiling as she felt herself fill with his hot cum, felt his thick shaft pulsate over and over and over again as he sprayed into her for what felt like a full minute.

Nathan collapsed limp on the bed, sweating and panting, his muscles sleek and pronounced, his cock throbbing inside of her. Cassandra rolled off of him, spreading her legs and checking her vagina: Nathan had came so deep inside her that nothing was leaking back out. She beamed with satisfaction.

"Hungry, baby?" she asked him, reaching for the cable phone on the nightstand.

Nathan nodded, rubbing his eyes. "Jesus..." he groaned, sitting up gingerly.

"Yes, room service?" she said into the phone. "Mmm-hmm? Oh well that won't do at all, I would like the full menu please. I don't care what time it is, I would like the full menu. I would like a filet and a side of mashed potatoes for me, and a hamburger with fries for my partner."

"Uh, could you make it a veggie burger?"

"Scratch that, a soy burger with fries. And a bottle of Verdeau, 1980. Thank you."

She hung up brusquely, rolling her eyes.

"They said we could order only soups and salads until 6am... not at the prices we're paying for this room we can!"

"I mean, I like me a salad."

"Nonsense. My little date needs his protein." She leaned over and kissed his cheek. "Or did you think you've blown your last load into me already?"

"Oh no, that pussy will make me cum until I fucking die."

"Well I'll try to stop early, then," she said with a wink, standing up and wrapping a silk bathrobe around her flushed naked body to answer the door when the food arrived.

They ate together at a table in the suite, the skyline gleaming through the wide wall-sized windows next to them. Cassandra had removed her bathrobe; they dined naked together.

"So, tell me about your children," Cassandra said, pouring him a glass of champagne.

"Sorry, my what?"

"You told me you were a father."

"Oh, right. Yeah, my first daughter is named Natalie, I had her when I was ten with my girlfriend in sixth grade."

"So she's about three right now. Was she named after you?"

"Yeah," he answered, chuckling and sipping the champagne. It was a startlingly smooth drink after the strong cocktails Cassandra had been mixing him so far.

"That was Maddie's idea," he continued. "She's the mother. And I had a daughter with my English teacher around the same time. Her name's Joy."

"Very cute. But it sounds like they're not the only ones."

"No... I don't know all their names, honestly. Some of them I've kept track of, some of them I haven't. Some I bet I don't even know about."

"Hmm." Cassandra nodded, taking a bite of her steak. "That makes sense. If you get me pregnant tonight, there's a fair chance you'll never know, huh?"

Nathan stared at her, chewing his burger. "Um... you can tell me if you want--"

Cassandra waved her hand dismissively. "Don't worry about that. I've got plenty of girlfriends who would love to help me raise her."

She reached across the table and took his hand.

"It's almost dawn," she said. "I want to make love to you on the balcony, to the sunrise. Then we can call it a night. Sound good?"

"Sounds fantastic!"

They finished their food, and Nathan followed Cassandra back into the bathroom to brush their teeth, sharing a toothbrush. Then she led him through the sliding glass window-doors, taking their champagne onto the balcony, where the warm salty sea air hit him as he stepped outside. The horizon was growing pink past the dark plane of the sea, but it was still dark enough that the city around them twinkled like stars. The balcony was unlit except by the light from inside; an array of cushy folding chairs was arranged between the two fancy potted ferns on either end of the platform.

"Give me that big fucking dick," Cassandra said sultrily, lowering her ass onto the chair, grabbing his cock and yanking it her direction, sticking it back into her wide-open mouth. Her hair was still tied back in a tight bun with no loose strands; Nathan reached down and played with her tits as she slid her lips and tongue back and forth along his shaft, jerking him with both her hands to match. He squeezed her soft breasts in his hand, feeling himself throb in her mouth as her warm lips and tongue churned up and down on him, his foreskin pulled back and his bare head rubbing directly on her swirling, slightly rough tongue. Even as he felt his tip pushing against the back of her throat, there was still plenty of length left for her two grip and jerk double-handed. She looked up at him as she sucked: her dark narrow eyes were enamored, infatuated even, but never submissive. Even as she groaned and slobbered across his cock, she was still the customer, and she was still in charge.

Nathan came hard again, his cum pulsing out, bursting in a pumping rhythm into her mouth. Like before, she swallowed it up gladly and rose to her feet in front of him, almost a full head taller. Nathan dove into her body face-first, hunching over to suck her nipples, wrapping his arms around her torso and sliding his tongue across her skin. Cassandra smiled serenely, looking down at him, letting him enjoy her body. His stiff cock pushed onto her thighs and her nipples tingled as he licked them and pulled on them between his lips.

"All right, stud," she said, ruffling his hair. "I want one last load in me. Let's get to it."

She pulled away from his worshipping hands and mouth and leaned naked against the balcony railing, sticking out her ass and spreading her legs apart for him. Nathan stood behind her, held his cock steady in his hand, pulled his foreskin back, and pushed into her soaking pussy.

He groaned loudly, all ten inches of his shaft gliding into her cunt. She moaned back, and he seized her hips, set his feet, and began to thrust, pounding her fast and deep with his full length. Ripples ran up her jiggling ass as he rammed himself into her over and over, and her hot wetness rubbed on his cock inside of her.

"I'm gonna cum inside of you, hun," Nathan growled as he pumped, but his voice was steady: it wasn't a warning, but a promise, and he kept on fucking her as the sun rose beyond the sea.

"Mmmm, I know, baby," Cassandra gasped breathlessly, and her voice _was_ strained as his cock pushed open her walls back and forth.

"Oh..." The pressure started to build in his large balls swinging under her vulva. " _Oh...!_ "

"Let it all out, give me that seed again, boy!"

"CASSANDRA!" Nathan cried out into the morning, and the sun flared into sight as he unleashed his cum and felt his balls drain deep into her cunt.

"Aaaah...!" he moaned, unable to hold himself back as his cock pulsated over and over inside of Cassandra. Even after he stopped thrusting, standing still balls-deep inside of her, breathing deep, he could feel the pulse of his shaft like a beating heart inside of her.

"Good GOD," Cassandra grunted, standing up straight as Nathan finally slid out of her, his cock hanging low between his thighs.

"Now that's more like it," she said, wiping sweat off her forehead and taking wobbly steps back towards the sliding glass doors. "Whoo... you made me cum, baby boy!"

Nathan followed her inside, and she collapsed onto the bed in front of him.

"I'm not much of a cuddler," she admitted, relaxing back against the pillows, pulling the sheets over her sweating nakedness. "But you can sleep with me if you want. My body is open to you until we wake up."

Nathan climbed into bed with her, draping his leg over her stomach, holding her tight, humping her slowly with his flaccid cock. He rested his face onto her bare breasts, and together they fell asleep.

When Nathan awoke, it was almost the afternoon, and Cassandra was gently prodding him awake. She was back in her all-black business suit, her hair down again like when he had met her.

"Baby boy," she said to him sweetly. "I have to go to work now, sweetie. Your money's on the dresser and I bought you some clothes and breakfast while you slept."

"Mmm... thanks," Nathan muttered groggily, rubbing his eyes.

Cassandra leaned over and gave him a warm goodbye kiss on the lips.

"Go fuck some more women, stud," she told him, heading to the door. "I'm rooting for you."

Cassandra left, and Nathan got out of bed, stretched, ate his breakfast and tried on his new clothes, then did as he had been told.


End file.
